(E)-2-decenyl chloride | 84988-53-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 英文名称: (E)-2-decenyl chloride
• 英文别名: (E)-1-chloro-2-decene；(E)-1-chlorodec-2-ene
• CAS: 84988-53-4
• 化学式: C₁₀H₁₉Cl
• 分子量: 174.714
• InChiKey: BFKFRIMTTLTFAY-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (E)-2-decenyl chloride 在 正丁基锂 、 四甲基乙二胺 、 四乙基对甲苯磺酸铵 作用下， 反应 8.0h， 生成 (E)-1,1-Dimethoxy-undec-3-ene
  参考文献：
  名称：

  New one carbon homologation reagents utilizing electrochemical oxidation of organosilicon compounds

  摘要：

  Phenylthio(trimethylsilyl)methane, phenylthiosbis(trimethylsily)methane, methoxy(trimethysily)methane, and methoxybis(trimethylsilyl)methane are depronated and the resulting anions are alkylated with electrophiles such as organic halides. The alkylation products are readily converted into the corresponding dimethyl acetals or methyl esters by electrochemical oxidation in methanol.

  DOI：

  10.1016/s0040-4020(01)87051-4
• 作为产物：
  描述：

  2-癸炔-1-醇 在 四氯化碳 、 lithium aluminium tetrahydride 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 (E)-2-decenyl chloride
  参考文献：
  名称：

  Chemoenzymatic Asymmetric Total Syntheses of Antitumor Agents (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and (R)- and (S)-Falcarinol from Panax ginseng Using an Enantioconvergent Enzyme-Triggered Cascade Reaction

  摘要：

  Total asymmetric synthesis of two components of Panax ginseng showing antitumor activity, i.e., (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and of both enantiomers of Falcarinol was accomplished. Due to the fact that the synthetic strategy was based on enantio-convergent biotransformations, the occurrence of any undesired stereoisomer was entirely avoided. The absolute configuration of naturally occurring Panaxytriol was confirmed to be (3R,9R,10R) on the basis of optical rotation values. It was shown that enzyme-triggered cascade reactions represent a valuable tool for the synthesis of natural products.

  DOI：

  10.1021/jo020073w

文献信息

• Nucleophilic Substitutions of Alcohols in High Levels of Catalytic Efficiency
  作者：Tanja Stach、Julia Dräger、Peter H. Huy

  DOI：10.1021/acs.orglett.8b01023

  日期：2018.5.18

  A practical method for the nucleophilic substitution (SN) of alcohols furnishing alkyl chlorides, bromides, and iodides under stereochemical inversion in high catalytic efficacy is introduced. The fusion of diethylcyclopropenone as a simple Lewis base organocatalyst and benzoyl chloride as a reagent allows notable turnover numbers up to 100. Moreover, the use of plain acetyl chloride as a stoichiometric

  介绍了一种在立体化学转化下以高催化效率对提供烷基氯化物，溴化物和碘化物的醇进行亲核取代（S N）的实用方法。二乙基环丙烯酮作为一种简单的路易斯碱有机催化剂与苯甲酰氯作为一种试剂的融合，可实现高达100的显着营业额。此外，首次证明了在转化型S N型转化中使用纯乙酰氯作为化学计量的促进剂。。操作上简单明了的协议展现出高水平的立体声选择性和可伸缩性，并且可以容忍各种功能组。
• α-Selective Allylation of Azo Compounds Using Allylic Barium Reagents
  作者：Akira Yanagisawa、Takuya Jitsukawa、Kazuhiro Yoshida

  DOI：10.1055/s-0032-1318306

  日期：——

  The addition of allylic barium reagents to azo compounds was achieved with high α-regioselectivity. The double-bond geometry of allylic barium reagents was retained throughout the reaction at –78 °C and E- or Z-enriched allylic hydrazines were selectively obtained from the corresponding allylic barium reagents. An allylic hydrazine was efficiently converted into an allylic amine by reductive N–N bond

  以高α-区域选择性将烯丙基钡试剂添加到偶氮化合物中。烯丙基钡试剂的双键几何结构在 –78 °C 的整个反应过程中保持不变，并且从相应的烯丙基钡试剂中选择性地获得富含 E 或 Z 的烯丙基肼。通过还原性 N-N 键断裂，烯丙基肼被有效地转化为烯丙基胺。
• Mechanistic Investigations of Palladium-Catalyzed Allylic Fluorination
  作者：Matthew H. Katcher、Per-Ola Norrby、Abigail G. Doyle

  DOI：10.1021/om401240p

  日期：2014.5.12

  A computational and experimental approach was employed to study the mechanism of the palladium(0)-catalyzed fluorination of allylic chlorides with AgF as fluoride source. Our findings indicate that an allylpalladium fluoride is a key intermediate necessary for the generation of both the nucleophile and electrophile. Evidence was also obtained to support a homobimetallic mechanism in which C–F bond

  采用计算和实验方法研究了以AgF为氟化物源的钯（0）催化烯丙基氯化物氟化的机理。我们的发现表明，烯丙基氟化钯是亲核试剂和亲电试剂均必需的关键中间体。还获得了支持同双金属机制的证据，其中中性烯丙基钯氟化物对阳离子烯丙基钯亲电试剂（以氟化物为抗衡离子）的亲核攻击发生了C-F键的形成。根据该机理和计算出的过渡态，对在区域选择性氟化中观察到的高支化选择性和异常配体效应进行了评估。这些结果可能对其他过渡金属催化的氟化机理具有重要意义。
• Regio- and Stereoselective Synthesis of 1,5-Dienes Using Allylic Barium Reagents
  作者：Akira Yanagisawa、Hiroaki Hibino、Shigeki Habaue、Yoshiyuki Hisada、Katsutaka Yasue、Hisashi Yamamoto

  DOI：10.1246/bcsj.68.1263

  日期：1995.5

  The highly α,α′ selective and stereocontrolled homocoupling reaction of allylic halides was achieved using barium reagent. The double-bond geometry of the starting allylic chloride was completely retained. The α,α′ cross-coupling products were also prepared stereospecifically and regioselectively by this method.

  使用钡试剂实现了烯丙基卤化物的高度α,α'选择性和立体控制的同偶联反应。完全保留了起始烯丙基氯的双键几何结构。α,α'交叉偶联产物也通过该方法立体定向和区域选择性制备。
• DIHYDROPYRONE COMPOUNDS AND HERBICIDES COMPRISING THE SAME
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：US20150299156A1

  公开（公告）日：2015-10-22

  The present invention provides a compound having an excellent efficacy for controlling weeds. A dihydropyrone compound of formula (I): wherein m is 1, 2 or 3; n is an integer of any one of 1 to 5; X represents O, S, S(O) or S(O) 2 ; R 1 represents a hydrogen atom or a methyl group; R 2 and R 3 represents a hydrogen atom, an C 1-6 alkyl group and the like; when X represents S, S(O) or S(O) 2 , R 4 represents an C 1-6 alkyl group, a C 1-6 haloalkyl group, an C 6-10 aryl group or a five- to six-membered heteroaryl group, and X represents O, S, S(O) or S(O) 2 , R 4 represents an C 6-10 aryl group or a five- to six-membered heteroaryl group; G represents a hydrogen atom and the like; Z represents a halogen atom, a cyano group, a nitro group, a phenyl group, an C 1-6 alkyl group and the like; is useful as an active ingredient for herbicides.

  本发明提供了一种具有优异除草效果的化合物。该化合物为式（I）的二氢吡酮化合物：其中m为1、2或3；n为1至5的任一整数；X代表O、S、S（O）或S（O）2；R1代表氢原子或甲基基团；R2和R3代表氢原子、C1-6烷基基团等；当X代表S、S（O）或S（O）2时，R4代表C1-6烷基基团、C1-6卤代烷基基团、C6-10芳基基团或五元至六元杂环芳基基团，当X代表O、S、S（O）或S（O）2时，R4代表C6-10芳基基团或五元至六元杂环芳基基团；G代表氢原子等；Z代表卤原子、氰基、硝基、苯基、C1-6烷基基团等。该化合物可用作除草剂的活性成分。