(+)-(S)-(Z)-4-Undecen-3-ol | 131831-41-9

• 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: (+)-(S)-(Z)-4-Undecen-3-ol
• 英文别名: (Z,3S)-undec-4-en-3-ol
• CAS: 131831-41-9
• 化学式: C₁₁H₂₂O
• 分子量: 170.295
• InChiKey: SYPSZWCYVFGEPS-JUDLJHIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  erythro-(αS,2R,3S)-3-Ethyl-α-n-hexyloxiranemethanol 在 4-二甲氨基吡啶 、 碲化氢 、 三乙基硼氢化锂 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (+)-(S)-(Z)-4-Undecen-3-ol
  参考文献：
  名称：

  Concomitant Epoxide Deoxygenation and Deacetylation of Glycidyl Acetates Induced by Telluride Ion

  摘要：

  Treatment of glycidyl acetates with telluride ion (Te2-) produced by reduction of elemental Te with LiEt(3)BH yields allylic alcohols by loss of the epoxide oxygen atom and the acetyl group from the ester. If the glycidyl acetate is disubstituted at C-3, a rearrangement to an isomeric allylic alcohol competes with the deoxygenation-deacetylation. Triethylborane, a byproduct in the reduction of Te, is believed to play an important role as a Lewis acid since when it is absent or removed by addition of fluoride ion the reaction is extremely slow.

  DOI：

  10.1021/jo00084a016

文献信息

• Enantioselective addition of (Z)- and (E)-alkenylzinc bromides to aldehydes: asymmetric synthesis of sec-allylalcohols
  作者：Wolfgang Oppolzer、Rumen N. Radinov

  DOI：10.1016/s0040-4039(00)93553-6

  日期：1991.10

  In situ prepared (Z)- and (E)-1-alkenylzinc bromides 5 were added to various aldehydes 1 in the presence of lithiated (+)-N-methylephedrine or (+)-2-(N,N-dimethylamino)-1,2-diphenylethanol to give sec. allyalcohols 7 in high optical purity with simple recovery of the chiral aminol 6.

  在锂化的（+）- N-甲基麻黄碱或（+）-2-（N，N-二甲基氨基）-的存在下，将原位制备的（Z）-和（E）-1-烯基溴化锌5添加到各种醛1中。 1,2-二苯乙醇给出sec。高光学纯度的烯丙基醇7与手性氨基6的简单回收。
• Kinetic resolution of racemic allylic alcohols by enantioselective epoxidation. A route to substances of absolute enantiomeric purity?
  作者：Victor S. Martin、Scott S. Woodard、Tsutomu Katsuki、Yasuhiro Yamada、Masonari Ikeda、K. Barry Sharpless

  DOI：10.1021/ja00410a053

  日期：1981.10
• Concomitant Epoxide Deoxygenation and Deacetylation of Glycidyl Acetates Induced by Telluride Ion
  作者：Donald C. Dittmer、Yanzhi Zhang、Robert P. Discordia

  DOI：10.1021/jo00084a016

  日期：1994.3

  Treatment of glycidyl acetates with telluride ion (Te2-) produced by reduction of elemental Te with LiEt(3)BH yields allylic alcohols by loss of the epoxide oxygen atom and the acetyl group from the ester. If the glycidyl acetate is disubstituted at C-3, a rearrangement to an isomeric allylic alcohol competes with the deoxygenation-deacetylation. Triethylborane, a byproduct in the reduction of Te, is believed to play an important role as a Lewis acid since when it is absent or removed by addition of fluoride ion the reaction is extremely slow.