ethyl 7-bromo-5-heptynoate | 63857-37-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 7-bromo-5-heptynoate
• 英文别名: ethyl 7-bromohept-5-ynoate
• CAS: 63857-37-4
• 化学式: C₉H₁₃BrO₂
• 分子量: 233.105
• InChiKey: GRLAEBXSCABFRI-UHFFFAOYSA-N

物化性质

• 沸点：
  266.2±25.0 °C(Predicted)
• 密度：
  1.316±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 7-bromo-5-heptynoate 生成 (Z)-7-[((E)-4-Hydroxy-non-2-enyl)-methanesulfonyl-amino]-hept-5-enoic acid
  参考文献：
  名称：

  11,12-Secoprostaglandins. 4. 7-(N-Alkylmethanesulfonamido)heptanoic acids

  摘要：

  A series of 7-(N-alkylmethanesulfonamido) heptanoic acids has been prepared which represents an extension of our 8-aza-11,12-secoprostaglandin studies. The studies. The compounds mimic the natural prostaglandins in that they markedly stimulate cAMP formation in the mouse ovary assay.

  DOI：

  10.1021/jm00220a014
• 作为产物：
  描述：

  7-(四氢吡喃氧基)-5-庚酸乙酯 在 溴 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以70%的产率得到ethyl 7-bromo-5-heptynoate
  参考文献：
  名称：

  Preparation of polyfunctional allenic alcohols by the regioselective addition of functionalized propargylic chromium(III) organometallics to carbonyl compounds

  摘要：

  The reaction of propargylic halides 1 (X = Cl, Br) with an aldehyde or ketone (0.67 equiv) in the presence of CrCl2 (2.0 equiv) and LiI (2 equiv, necessary if X = Cl) affords allenic alcohols 3 with excellent regioselectivities (3-6% of the regioisomeric acetylenic alcohol 4 is formed) and in good yields (68-90%). Interestingly, this method allows the generation of highly functionalized intermediate propargylic chromium organometallics contained an ester, cyano, or chloride functionality. The alpha-alkyl-substituted propargylic bromide 10 reacts with benzaldehyde yielding the acetylenic alcohol 11 as a diastereomeric mixture of only one regioisomer (90% yield).

  DOI：

  10.1021/jo00041a006

文献信息

• Regioselective Transition-Metal-Free Allyl-Allyl Cross-Couplings
  作者：Mario Ellwart、Ilya S. Makarov、Florian Achrainer、Hendrik Zipse、Paul Knochel

  DOI：10.1002/anie.201603923

  日期：2016.8.22

  Readily prepared allylic zinc halides undergo SN2‐type substitutions with allylic bromides in a 1:1 mixture of THF and DMPU providing 1,5‐dienes regioselectively. The allylic zinc species reacts at the most branched end (γ‐position) of the allylic system furnishing exclusively γ,α′‐allyl–allyl cross‐coupling products. Remarkably, the double bond stereochemistry of the allylic halide is maintained during

  现成的烯丙基卤化锌在THF和DMPU的1：1混合物中用烯丙基溴进行S N 2型取代，可选择性地提供1,5二烯。烯丙基锌物种在烯丙基体系的最分支末端（γ位置）反应，专门提供γ，α'-烯丙基-烯丙基交叉偶联产物。值得注意的是，烯丙基卤的双键立体化学在交叉偶联过程中得以保持。还可以耐受几个官能团（酯，腈）。烯丙基锌试剂的这种交叉偶联可以扩展到炔丙基和苄基卤化物。DFT计算显示了氯化锂在该替代中的重要性。
• 16-Ethers of 8-aza-9-dioxothia-11,12-seco-prostaglandins
  申请人：Merck & Co., Inc.

  公开号：US03991106A1

  公开（公告）日：1976-11-09

  The invention is concerned with novel 16-aryloxy-, 16-alkoxy-, 16-arylthio- and 16-alkylthio-8-aza-9-dioxothia-11,12-seco-prostaglandins and processes for their preparation. These novel compounds are useful as pharmaceuticals since they can be used in animals for estrus synchronization and treatment of infertility due to persistence of luteal function.

  本发明涉及新型的16-芳氧基、16-烷氧基、16-芳硫基和16-烷硫基-8-氮杂-9-二氧硫-11,12-环丙孕酮类化合物及其制备方法。这些新型化合物可作为药物使用，因为它们可用于动物的发情同步和治疗黄体功能持续引起的不育症。
• 11,12-Seco-prostaglandins
  申请人：Merck & Co., Inc.

  公开号：US04055596A1

  公开（公告）日：1977-10-25

  The invention is concerned with novel 16-aryloxy-, 16-alkoxy-, 16-arylthio- and 16-alkylthio-8-aza-9-dioxothia-11,12-seco-prostaglandins and processes for their preparation. These novel compounds are useful as pharmaceuticals since they can be used in animals for estrus synchronization and treatment of infertility due to persistence of luteal function.

  该发明涉及一种新型的16-芳氧基、16-烷氧基、16-芳硫基和16-烷硫基-8-氮杂-9-二氧硫-11,12-去环前列腺素以及它们的制备方法。这些新型化合物可用作药物，因为它们可用于动物的发情同步和治疗黄体功能持续引起的不孕症。
• Hydantoins and thiohydantoins, process for their preparation and pharmaceutical compositions containing them
  申请人：BEECHAM GROUP PLC

  公开号：EP0006352A1

  公开（公告）日：1980-01-09

  A compound of the formula (I): wherein: XisOorS; Y is-CH-CH-or-C≡C-; n is 1 to 5; R, is hydrogen or CO2R1 represents an ester group in which the R, moiety contains from 1 to 12 carbon atoms; R2 is hydrogen or C1-4 alkyl; R3 is hydroxy or protected hydroxy; R4 is C1-9 alkyl, C3-8 cycloalkyl or C3-8 cycloalky-C1-6 alkyl; or Rz and R4 taken with the carbon atom to which they are joined represent a C5-8 cycloalkyl group; and Rs is C1-6 alkyl substituted by one nitro, hydroxy, C1-6 alkoxy, CO2A, (CO2A)2, CN or halogen group; C5-8 cycloalkyl; or CO2A; in R5 when present A is hydrogen or CO2A represents an ester group in which the A moiety contains from 1 to 12 carbon atoms; and salts thereof; has useful pharmaceutical activity, including bronchodilator activity.

  式 (I) 的化合物： 其中 XisOorS； Y 是-CH-CH-或-C≡C-； n 是 1 至 5； R，是氢或 CO2R1 代表酯基，其中 R，分子含有 1 至 12 个碳原子； R2 是氢或 C1-4 烷基； R3 是羟基或受保护的羟基； R4 是 C1-9 烷基、C3-8 环烷基或 C3-8 环烷基-C1-6 烷基；或 Rz 和 R4 与它们连接的碳原子一起代表 C5-8 环烷基；以及 Rs是被一个硝基、羟基、C1-6烷氧基、CO2A、(CO2A)2、CN或卤素基团取代的C1-6烷基；C5-8环烷基；或CO2A；在R5中，当存在时A是氢或CO2A代表酯基，其中A分子含有1至12个碳原子；及其盐类；具有有用的药物活性，包括支气管扩张剂活性。
• US3991106A
  申请人：——

  公开号：US3991106A

  公开（公告）日：1976-11-09