(E)-1-chlorodec-1-en-3-one | 67356-46-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1-chlorodec-1-en-3-one
• 英文别名: trans-1-Chloro-dec-1-en-3-one
• CAS: 67356-46-1
• 化学式: C₁₀H₁₇ClO
• 分子量: 188.697
• InChiKey: BEBLXWVFJRCWCM-CMDGGOBGSA-N

物化性质

• 沸点：
  255.7±23.0 °C(Predicted)
• 密度：
  0.964±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-1-chlorodec-1-en-3-one 在 sodium hydroxide 作用下， 生成 2-壬酮
  参考文献：
  名称：

  Wakayama; Maekawa, Kogyo Kagaku zasshi / Journal of the Society of Chemical Industry, 1955, vol. 58, p. 716

  摘要：

  DOI：
• 作为产物：
  描述：

  dec-1-yn-3-ol 在 Jones reagent 、 三氟乙酸 、 lithium chloride 作用下， 以 异丙醇 、 丙酮 为溶剂， 反应 1.0h， 生成 (E)-1-chlorodec-1-en-3-one
  参考文献：
  名称：

  Selective Activation/Coupling of Polyhalogenated Nucleophiles in Ni/Cr-Mediated Reactions: Synthesis of C1–C19 Building Block of Halichondrin Bs

  摘要：

  The C1-C19 building block 46 of halichondrin Bs was synthesized via a selective activation/coupling of beta-bromoenone 34 with aldehyde 35 in a Ni/Cr-mediated reaction. The first phase of study was a method development to effect a coupling of a naked vinylogous anion with an aldehyde. The study with the coupling of 9 + 10 -> 11 revealed: (1) beta-bromoenone 9b is a better nucleophile than the corresponding beta-iodo- and beta-chloroenones 9a,c; (2) (Me)(2)Phen(OMe)(2)center dot NiCl2 13b is a better Ni-catalyst than (Me)(2)Phen(H)(2)center dot NiCl2 13a; and (3) a low Ni-catalyst loading, for example, 0.05-0.1 mol % Ni-catalyst against 10 mol % Cr-catalyst, is crucial for an effective coupling. The second phase of study was a method development to realize a selective activation/coupling of polyhalogenated nucleophiles such as 34. The competition experiment of 10 + 9b over 10 + 31a-c revealed: (1) (Me)(2)Phen(OMe)(2)center dot NiCl2 13b is more effective than (Me)(2)Phen(H)(2)center dot NiCl2 13a for the required selective activation/coupling; (2) a low Ni-catalyst loading, for example, 0.05-0.1 mol % Ni-catalyst against 10 mol % Cr-catalyst, is crucial for discriminating beta-bromoenone 9b from the three types of vinyl iodides 31a-c. The third phase of study was an application of the developed method to execute the proposed coupling of 34 + 35 -> 36. For this application, a polyether-type Ni-catalyst 37c, readily soluble in the reaction medium, was introduced to achieve the selective activation/coupling with higher efficiency. With use of ion-exchange resin-based device, the coupling product 36 was transformed to the C1-C19 building block 46 of halichondrin Bs without purification/separation of the intermediates.

  DOI：

  10.1021/jacs.5b03498

文献信息

• Ketovinylation of β-dicarbonyl compounds
  作者：N.K. Kochetkov、L.J. Kudryashov、B.P. Gottich

  DOI：10.1016/0040-4020(61)80100-2

  日期：1961.1

  labile hydrogens results in the formation of complex mixtures. Ethyl malonate and ethyl acetoacetate have, however, been successfully ketovinylated. In the former case, α-carbethoxy-δ-keto-β,γ-unsaturated acids are produced in high yield and depending on the conditions of ketovinylation of ethyl acetoacetate either 4-alkyl salicyclic acids or polysubstituted benzene derivatives may be prepared. Further,

  通常仅用一个不稳定的氢将酮乙烯基引入β-二羰基化合物中，但是存在两个不稳定的氢会导致形成复杂的混合物。然而，丙二酸乙酯和乙酰乙酸乙酯已被成功酮化。在前一种情况下，高产率地生产α-乙氧基-δ-酮基-β，γ-不饱和酸，并且根据乙酰乙酸乙酯的酮乙烯基化的条件，可以制备4-烷基水杨酸或多取代的苯衍生物。此外，丙二酸乙酯和乙酰乙酸烷基酯的酮乙烯基化产物可用于合成（1）不饱和脂族酮酸或二酮或（2）多种α-吡喃酮衍生物。提出了乙酰乙酸乙酯的酮乙烯基化机理，并提出了反式 建立了酮乙烯基化产品的构型。
• Influence of aestivation on the survival of Galba truncatula (Mollusca : Gasteropoda) populations according to altitude
  作者：M. D. Goumghar、D. Rondelaud、G. Dreyfuss、M. Benlemlih

  DOI：10.1051/limn/2001018

  日期：2001.9

  Field and laboratory studies on 11 populations of Galba truncatula were performed to determine the survival rate of snails after aestivation, to specify the range of their shell heights, and to establish the percentage of G. truncatula which burrowed in soil when summer drying occurred. These investigations were performed using six lowland populations living in central France (alt. 206-282 m) and five highland populations, located in the Massif central (alt. 806-900 m). The survival rate of G. truncatula after flooding dried soil with water was significantly higher in the highland than in the lowland populations (69.5-80.7 % in road ditches, for example, instead of 29.3-33.0%). The mean shell heights of surviving snails and the durations of snail re-activation in water did not show any significant variation, whatever the origin of snail population. The percentages of snails buried in drying soil were higher in the highland population (13.0 % and 15.0 % of juvenile snails, for example, instead of 4.0 % and 7.7 % in lowland snails). In the lowland population only young snails buried, whereas 5.8-8.3 % of adults in the highland population were partially burrowing. The local climate of the sites studied in the Massif central, and the ability of snails to burrow into the mud when stagnant water disappeared in July, might explain the higher survival rate during aestivation.

  对11个Galba truncatula种群进行的野外和实验室研究旨在确定蜗牛在夏季休眠后的存活率，明确其壳高范围，并确定在夏季干旱发生时有多少G. truncatula会在土壤中埋藏。这些研究在法国中部的六个低地种群（海拔206-282米）和位于中央高地的五个高地种群（海拔806-900米）进行。G. truncatula在淹水干土后存活率在高地种群中显著高于低地种群（例如，在道路排水沟中为69.5-80.7%，而低地为29.3-33.0%）。存活蜗牛的平均壳高和在水中重新活化的持续时间无论蜗牛种群的来源如何均未显示显著差异。在干燥的土壤中埋藏的蜗牛比例在高地种群中更高（例如，青少年蜗牛埋藏率为13.0%和15.0%，而低地蜗牛为4.0%和7.7%）。在低地种群中只有年轻蜗牛会埋藏，而在高地种群中有5.8-8.3%的成年蜗牛是部分埋藏的。研究中高地的当地气候和蜗牛在静水消失后能够埋入泥土的能力，可能解释了其在夏季休眠期间更高的存活率。
• Prostaglandin derivatives
  申请人：Gist Brocades N.V.

  公开号：US04164446A1

  公开（公告）日：1979-08-14

  Novel 18.xi.-, 19.xi.- and 20.xi.-hydroxy-prostaglandin derivatives of the formula I ##STR1## wherein the dotted line in the position 8-12 indicates the optional presence of a double bond, the waved lines in position 15 indicate that the hydroxyl group and the group R.sub.4 are either in .alpha.- or .beta.-position and Z represents a --CH.sub.2 CH.sub.2 -- or a cis --CH.dbd.CH--group, and wherein R represents one of the groups: ##STR2## (wherein the waved lines indicate that the hydroxyl groups are either in .alpha.- or .beta.-position and R.sub.1 represents a hydrogen atom, a methyl or ehtyl group), R.sub.2 represents either an oxygen atom or a hydrogen atom and an .alpha.- or .beta.-hydroxyl group, R.sub.3 represents a hydrogen atom or a hydroxyl group and R.sub.4 represents a hydrogen atom or a methyl group, with the proviso that when simultaneously, R.sub.1, R.sub.3 and R.sub.4 each represents a hydrogen atom, R.sub.2 represents an oxygen atom, a double bond is in 8-12 position and the 15-hydroxyl group is in position .alpha., R does not represent the group (b), but that when in addition to these conditions, Z represents a cis --CH.dbd.CH--group and the 8-12 position is saturated, R either represents the groups (b) or (c); and the pharmaceutically acceptable salts and esters thereof, novel process for their preparation by selective microbiological hydroxylation of compounds of formula II ##STR3## wherein the dotted line in the position 10-11 indicates the optional presence of a double bond in case the 8-12 position is saturated and the other symbols are as defined hereinabove, by means of microorganisms of the Division of Eumycota or, as far as the introduction of a hydroxyl group in the 18- or 19-position is concerned, of the Family of Streptomycetaceae, and, if desired, conversion of the 18.xi.-, 19.xi.- and 20.xi.-hydroxy-prostaglandin derivatives thus obtained into pharmaceutically acceptable salts and esters thereof, and pharmaceutical compositions containing at least one of the novel hydroxy-prostaglandin derivatives of formula I.

  18.xi.-、19.xi.-和20.xi.-羟基前列腺素衍生物的化学式I如下：##STR1## 其中，位置8-12的虚线表示双键的可选存在，位置15的波浪线表示羟基和R.sub.4基团可以是.alpha.或.beta.位置，Z代表--CH.sub.2 CH.sub.2 --或顺式--CH.dbd.CH--基团，R代表以下基团之一：##STR2##（其中，波浪线表示羟基可以是.alpha.或.beta.位置，R.sub.1代表氢原子、甲基或乙基基团，R.sub.2代表氧原子或氢原子和.alpha.或.beta.羟基，R.sub.3代表氢原子或羟基，R.sub.4代表氢原子或甲基基团，但是当同时，R.sub.1、R.sub.3和R.sub.4各代表氢原子，R.sub.2代表氧原子，8-12位置存在双键，15-羟基位于.alpha.位置时，R不代表(b)基团，但是当除此之外，Z代表顺式--CH.dbd.CH--基团且8-12位置饱和时，R代表(b)或(c)基团；以及其药学上可接受的盐和酯，通过化合物II的选择性微生物羟化制备它们的新方法如下：##STR3## 其中，位置10-11的虚线表示8-12位置饱和时双键的可选存在，其他符号如上所述，通过真菌界或者在引入18-或19-羟基时，通过链霉菌科的微生物进行，如果需要，将得到的18.xi.-、19.xi.-和20.xi.-羟基前列腺素衍生物转化为药学上可接受的盐和酯，并含有至少一种新型羟基前列腺素衍生物的药物组合物。
• Carnation plant named ‘Hilbechgre’
  申请人：Koekkoek Arthur N. J.

  公开号：USPP030287P3

  公开（公告）日：2019-03-12

  A new and distinct cultivar of Carnation plant named ‘Hilbechgre’, characterized by its compact, uniformly mounding and upright to broadly spreading plant habit; relatively small leaves; freely flowering habit; light yellow-colored double flowers with red purple-colored margins and apices; and good container and garden performance.

  一种新的石竹植物品种命名为“Hilbechgre”，其特征为紧凑、均匀的丘状植物习性，直立到广泛扩展；相对较小的叶子；自由开花的习性；浅黄色的双重花朵，带有红紫色的边缘和顶端；以及良好的盆栽和花园表现。
• 18 OR 19 Hydroxy prostaglandins
  申请人：Gist-Brocades N.V.

  公开号：US04054595A1

  公开（公告）日：1977-10-18

  Novel 18 -, 19 - and 20 -hydroxy-prostaglandin derivatives of the formula I ##STR1## wherein the dotted line in the position 8-12 indicates the optional presence of a double bond, the waved lines in position 15 indicate that the hydroxyl group and the group R.sub.4 are either in .alpha.- or .beta.-position and Z represents a -- CH.sub.2 CH.sub.2 -- or a cis -- CH=CH -- group, and wherein R represents one of the groups: ##STR2## (wherein the waved lines indicate that the hydroxyl groups are either in .alpha.- or .beta.-position and R.sub.1 represents a hydrogen atom, a methyl or ethyl group), R.sub.2 represents either an oxygen atom or a hydrogen atom and an .alpha.- or .beta.-hydroxyl group, R.sub.3 represents a hydrogen atom or a hydroxyl group and R.sub.4 represents a hydrogen atom or a methyl group, with the proviso that when simultaneously, R.sub.1, R.sub.3 and R.sub.4 each represents a hydrogen atom, R.sub.2 represents an oxygen atom, a double bond is in 8-12 position and the 15-hydroxyl group is in position .alpha., R does not represent the group (b), but that when in addition to these conditions, Z represents a cis -- CH=CH -- group and the 8-12 position is saturated, R either represents the groups (b) or (c); and the pharmaceutically acceptable salts and esters thereof, novel process for their preparation by selective microbiological hydroxylation of compounds of formula II ##STR3## wherein the dotted line in the position 10-11 indicates the optional presence of a double bond in case the 8-12 position is saturated and the other symbols are as defined hereinabove, by means of microorganisms of the Division of Eumycota or, as far as the introduction of a hydroxyl group in the 18- or 19-position is concerned, of the Family of Streptomycetaceae, and, if desired, conversion of the 18 -, 19 - and 20 -hydroxy-prostaglandin derivatives thus obtained into pharmaceutically acceptable salts and esters thereof, and pharmaceutical compositions containing at least one of the novel hydroxy-prostaglandin derivatives of formula I.

  18-, 19-和20-羟基前列腺素衍生物的化学式为I，其中8-12位置的虚线表示双键的可选存在，15位置的波浪线表示羟基和R.sub.4基团可以是α或β位，Z代表-CH.sub.2 CH.sub.2-或顺式-CH=CH-基团，而R代表以下一种基团：其中波浪线表示羟基可以是α或β位，R.sub.1代表氢原子、甲基或乙基基团，R.sub.2代表氧原子或氢原子和α或β-羟基基团，R.sub.3代表氢原子或羟基基团，R.sub.4代表氢原子或甲基基团，但是当同时R.sub.1、R.sub.3和R.sub.4各代表氢原子时，R.sub.2代表氧原子，8-12位置存在双键，15-羟基位于α位置时，R不代表(b)基团，但是当除此之外，Z代表顺式-CH=CH-基团且8-12位置饱和时，R代表基团(b)或(c)；以及其药学上可接受的盐和酯，通过选择性微生物羟化化合物II的新过程制备，其中10-11位置的虚线表示8-12位置饱和时双键的可选存在，其他符号如上所定义，通过真菌门或者在引入18-或19-位置的羟基时，通过链霉菌科的微生物进行，如果需要，将得到的18-、19-和20-羟基前列腺素衍生物转化为药学上可接受的盐和酯，以及含有至少一种新的化学式I羟基前列腺素衍生物的药物组合物。