十二碳-1,11-二烯-3-醇 | 81943-76-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 十二碳-1,11-二烯-3-醇
• 英文名称: 1,11-dodecadien-3-ol
• 英文别名: dodeca-1,11-dien-3-ol
• CAS: 81943-76-2
• 化学式: C₁₂H₂₂O
• 分子量: 182.306
• InChiKey: UTIVIZWMQSJSNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  13
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  十二碳-1,11-二烯-3-醇 在 ruthenium trichloride 、 lithium hydroxide 、 sodium periodate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 30.0h， 生成 2-羟基癸二酸
  参考文献：
  名称：

  一种方便的合成羟基二酸的通用方法

  摘要：

  带有末端双键的烯烃醛和环氧化物与格氏试剂反应，由所得醇制得的乙酸酯在NaIO 4存在下用RuCl 3 · x H 2 O处理后进行双键裂解，生成乙酰氧基二酸。然后用LiOH水解得到羟基二酸。

  DOI：

  10.1016/j.tetlet.2007.03.053
• 作为产物：
  描述：

  9-十烯-1-醇 在 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 十二碳-1,11-二烯-3-醇
  参考文献：
  名称：

  双环大环内酯-丁烯内酯核心结构的中继开环/双环复分解策略†

  摘要：

  已经开发出一种简洁的策略来合成各种天然产物的双环大环内酯-丁烯内酯核心结构，其大环内酯环的大小为12至16元。双环结构易于使用中继开环/双环复分解策略进行组装。作为该策略的应用，已经实现了（±）-去甲基曼舒洛尔的有效合成。

  DOI：

  10.1039/c4ra10937f

文献信息

• Direct Oxidative Heck Cyclizations: Intramolecular Fujiwara-Moritani Arylations for the Synthesis of Functionalized Benzofurans and Dihydrobenzofurans
  作者：Haiming Zhang、Eric M. Ferreira、Brian M. Stoltz

  DOI：10.1002/anie.200461294

  日期：2004.11.19
• Synthesis and use of the n-bromododecane-1,12-diols as conformational probes for general anesthetic target sites
  作者：R. Dickinson、E. H. Smith、N. P. Franks、W. R. Lieb

  DOI：10.1021/jm00053a014

  日期：1993.1

  The n-bromododecane-1,12-diols with bromine on carbons 2,3,5, and 6, respectively, were synthesized and found to be potent general anesthetics. They were also found to be potent inhibitors of firefly luciferase, a protein model for the primary target sites underlying general anesthesia. However, their effects on lipid bilayers were small, lowering the chain-melting phase transition temperature by less than l-degrees-C at their EC50 concentrations for general anesthesia. A large dependence upon the position of the bromine atom was found for both n-hexadecane/water partition coefficients and inhibition constants for firefly luciferase; a much smaller positional dependence was found for induction of general anesthesia and for disrupting lipids. These results are consistent with the bulky bromine atom inhibiting the conformational flexibility of the diol hydrocarbon chain, making these bromo diols useful probes for ascertaining the shapes of apolar binding sites. In particular, our measurements suggest that these novel anesthetics produce general anesthesia by binding to long and relatively narrow apolar target sites in the central nervous system.
• A relay ring-opening/double ring-closing metathesis strategy for the bicyclic macrolide-butenolide core structures
  作者：Mahesh B. Halle、Rodney A. Fernandes

  DOI：10.1039/c4ra10937f

  日期：——

  been developed for the synthesis of the bicyclic macrolide-butenolide core structures of various natural products with the macrolide ring size ranging from 12- to 16-membered. The bicyclic structure was easily assembled using the relay ring-opening/double ring-closing metathesis strategy. An efficient synthesis of (±)-desmethyl manshurolide has been achieved as an application of this strategy.

  已经开发出一种简洁的策略来合成各种天然产物的双环大环内酯-丁烯内酯核心结构，其大环内酯环的大小为12至16元。双环结构易于使用中继开环/双环复分解策略进行组装。作为该策略的应用，已经实现了（±）-去甲基曼舒洛尔的有效合成。
• A convenient general method for the synthesis of hydroxy diacids
  作者：Chandramouli Chiruta、Santosh Jachak、Derrick L.J. Clive

  DOI：10.1016/j.tetlet.2007.03.053

  日期：2007.4

  Olefinic aldehydes and epoxides with terminal double bonds react with Grignard reagents, and the acetates made from the resulting alcohols undergo double bond cleavage on treatment with RuCl3·xH2O in the presence of NaIO4 to give acetoxy diacids. Hydrolysis with LiOH then affords hydroxy diacids.

  带有末端双键的烯烃醛和环氧化物与格氏试剂反应，由所得醇制得的乙酸酯在NaIO 4存在下用RuCl 3 · x H 2 O处理后进行双键裂解，生成乙酰氧基二酸。然后用LiOH水解得到羟基二酸。