(S,Z)-5,9-dimethyldeca-4,8-dien-3-ol | 1344731-19-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (S,Z)-5,9-dimethyldeca-4,8-dien-3-ol
• 英文别名: (Z)-5,9-dimethyldeca-4,8-dien-(S)-3-ol；(3S,4Z)-5,9-dimethyldeca-4,8-dien-3-ol
• CAS: 1344731-19-6
• 化学式: C₁₂H₂₂O
• 分子量: 182.306
• InChiKey: PQUSMVMWVMGVGN-MMRAYRKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  13.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (S,Z)-5,9-dimethyldeca-4,8-dien-3-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 三异丙氧基氯化钛 、 戴斯-马丁氧化剂 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.67h， 生成 (R)-4-methyl-4-(4-methylpent-3-en-1-yl)cyclohex-2-en-1-one
  参考文献：
  名称：

  烯丙醇的立体选择性烷基化：串联乙氧基化和功能化

  摘要：

  一种多功能正式小号Ñ 2'烯丙基醇的烷基化已被Kulinkovich试剂的装置和在与亲电子推定alkyltitanium中间体的原位阐述设计（参见方案）。该方法的效用已在全碳四元中心的立体选择性构造中得到证明。

  DOI：

  10.1002/anie.201104331
• 作为产物：
  描述：

  ethyl-nerol 在 硼烷-N,N-二乙基苯胺 、 四丙基高钌酸铵 、 N-甲基吗啉氧化物 、 (S)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 11.0h， 生成 (S,Z)-5,9-dimethyldeca-4,8-dien-3-ol 、 (R,Z)-5,9-dimethyldeca-4,8-dien-3-ol
  参考文献：
  名称：

  Allylic Substitution for Construction of a Chiral Quaternary Carbon Possessing an Aryl Group

  摘要：

  Phenylcopper reagents derived from 2:1 PhMgBr/Cu(acac)(2) and 3:1:1 PhMgBr/Cu(acac)(2)/ZnI2 were found to be highly reactive and regioselective in the allylic substitution of gamma,gamma-disubstituted secondary allylic picolinates designed for construction of a quaternary carbon, whereas the previous 2:1 ArMgBr/CuBr center dot Me2S reagent and that with ZnX2 were unsuccessful. The generality of the ArMgBr/Cu(acac)(2) reagent was examined with enantiomerically enriched allylic picolinates, which furnished quaternary carbons with high efficiency in >92% regioselectivity and >97% chirality transfer. Two cyclohexanes with a quaternary carbon were synthesized by using these reagents.

  DOI：

  10.1021/jo400248y

文献信息

• Allylic Substitution for Construction of a Chiral Quaternary Carbon Possessing an Aryl Group
  作者：Chao Feng、Yuichi Kobayashi

  DOI：10.1021/jo400248y

  日期：2013.4.19

  Phenylcopper reagents derived from 2:1 PhMgBr/Cu(acac)(2) and 3:1:1 PhMgBr/Cu(acac)(2)/ZnI2 were found to be highly reactive and regioselective in the allylic substitution of gamma,gamma-disubstituted secondary allylic picolinates designed for construction of a quaternary carbon, whereas the previous 2:1 ArMgBr/CuBr center dot Me2S reagent and that with ZnX2 were unsuccessful. The generality of the ArMgBr/Cu(acac)(2) reagent was examined with enantiomerically enriched allylic picolinates, which furnished quaternary carbons with high efficiency in >92% regioselectivity and >97% chirality transfer. Two cyclohexanes with a quaternary carbon were synthesized by using these reagents.
• Stereoselective Alkylation of Allylic Alcohols: Tandem Ethylation and Functionalization
  作者：Pragna Pratic Das、Ivan L. Lysenko、Jin Kun Cha

  DOI：10.1002/anie.201104331

  日期：2011.9.26

  A versatile formal SN2′ alkylation of allylic alcohols has been devised by means of the Kulinkovich reagent and in situ elaboration of the presumed alkyltitanium intermediates with electrophiles (see scheme). The utility of this method has been demonstrated in the stereoselective construction of all‐carbon quaternary centers.

  一种多功能正式小号Ñ 2'烯丙基醇的烷基化已被Kulinkovich试剂的装置和在与亲电子推定alkyltitanium中间体的原位阐述设计（参见方案）。该方法的效用已在全碳四元中心的立体选择性构造中得到证明。