(E)-1-acetoxy-3,7-dimethylhept-2-ene | 70795-75-4

• 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: (E)-1-acetoxy-3,7-dimethylhept-2-ene
• 英文别名: 1-acetoxy-3,7-dimethyloct-2(E)-ene；6,7-dihydrogeranyl acetate；dihydrogeranyl acetate；acetic acid-(3,7-dimethyl-oct-2t-enyl ester)；Essigsaeure-(3,7-dimethyl-oct-2t-enylester)；(E)-3,7-dimethyloct-2-enyl acetate；3,7-Dimethyloct-2-enyl acetate；[(E)-3,7-dimethyloct-2-enyl] acetate
• CAS: 70795-75-4
• 化学式: C₁₂H₂₂O₂
• 分子量: 198.305
• InChiKey: LZLOAANJNAQPIH-DHZHZOJOSA-N

物化性质

• 保留指数：
  1332.2

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  (E)-1-acetoxy-3,7-dimethylhept-2-ene 、 炔丙基丙二酸二甲酯 在 四(三苯基膦)钯 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 methyl 5,9-dimethyl-2-(methoxycarbonyl)-2-propyn-3-yl-4(E)-decenoate
  参考文献：
  名称：

  金属催化与热烯反应在区域选择性上的不寻常二分法

  摘要：

  1，6-烯炔的Pd（+2）催化环化反应是热Alder烯反应的补充；提出了调用远程绑定位点的原理。

  DOI：

  10.1016/s0040-4039(00)94977-3
• 作为产物：
  描述：

  7-chloro-3,7-dimethyl-2E-octen-1-yl acetate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 以93%的产率得到(E)-1-acetoxy-3,7-dimethylhept-2-ene
  参考文献：
  名称：

  On the selective reduction of the distal olefin in geraniol and farnesol derivatives

  摘要：

  The selective reduction of the distal olefin of many types of terpenoid-based natural products has been commonly approached using gaseous HCl in CH2Cl2. We herein present evidence that this method is inefficient and produces many side products. whose formation. ill our hands, was difficult to avoid (over several reaction runs). A more efficient procedure for geranyl acetate using 1 equiv. of TiCl4 in CH(2)Cl2 at -78degreesC is reported. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01047-5

文献信息

• Selective reduction of the distant double bond(s) in geranyl, farnesyl and geranyl geranyl derivatives
  作者：Marc Julia、Pierre Roy

  DOI：10.1016/s0040-4020(01)88050-9

  日期：1986.1

  Selective addition of hydrogen chloride on the non-proximal double bond(s) of the title compounds followed by hydrogenolysis led to selective hydrogenation of these double bond(s).

  在标题化合物的非最接近的双键上选择性地添加氯化氢，然后进行氢解，导致这些双键的选择性加氢。
• An unusual dichotomy in the regioselectivity of a metal catalyzed versus thermal ene reaction
  作者：Barry M. Trost、Mark Lautens

  DOI：10.1016/s0040-4039(00)94977-3

  日期：1985.1

  A Pd(+2) catalyzed cyclization of a 1,6-enyne complements a thermal Alder ene reaction; a rationale invoking a remote binding site is proposed.

  1，6-烯炔的Pd（+2）催化环化反应是热Alder烯反应的补充；提出了调用远程绑定位点的原理。
• Carboxylic acid esters of cis-3, 7-dimethyl-2-octen-1-ol
  申请人：HOFFMANN LA ROCHE

  公开号：US02833811A1

  公开（公告）日：1958-05-06
• On the selective reduction of the distal olefin in geraniol and farnesol derivatives
  作者：Alexandre Demotie、Ian J.S. Fairlamb、Sally K. Radford

  DOI：10.1016/s0040-4039(03)01047-5

  日期：2003.6

  The selective reduction of the distal olefin of many types of terpenoid-based natural products has been commonly approached using gaseous HCl in CH2Cl2. We herein present evidence that this method is inefficient and produces many side products. whose formation. ill our hands, was difficult to avoid (over several reaction runs). A more efficient procedure for geranyl acetate using 1 equiv. of TiCl4 in CH(2)Cl2 at -78degreesC is reported. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Trost, Barry M.; Lautens; Chan, Journal of the American Chemical Society, 1991, vol. 113, # 2, p. 636 - 644
  作者：Trost, Barry M.、Lautens、Chan、Jebaratnam、Mueller

  DOI：——

  日期：——