3-methylene-6-hepten-1-ol | 208766-08-9

• 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: 3-methylene-6-hepten-1-ol
• 英文别名: 3-Methylidenehept-6-en-1-ol
• CAS: 208766-08-9
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: AGVSLWNSTURZLY-UHFFFAOYSA-N

物化性质

• 沸点：
  183.4±9.0 °C(predicted)
• 密度：
  0.852±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  3-methylene-6-hepten-1-ol 在 lithium aluminium tetrahydride 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 77.0h， 生成 methyl (6R)-6,7-dihydroxy-4-oxoheptanoate
  参考文献：
  名称：

  Synthesis of a Butyrolactone Precursor of an Algae Nonaether from an Enantiopure Glycol Obtained by Hoppe's Chemistry

  摘要：

  Homoallyl carbamate 20, (-)-sparteine, and sBuLi gave a lithium derivative which was formylated with DMF giving the crude aldehydocarbamate 19. With Lithium aluminum hydride in refluxing THF, this compound provided diol 22 in 90% overall yield and with 96% ee. This material was carried on to the gamma-lactone monoethers 13 (benzyl ether) or 14 (trityl ether). These compounds should be precursors for synthesizing the naturally occurring nonaether 7.

  DOI：

  10.1002/(sici)1099-0690(199806)1998:6<1023::aid-ejoc1023>3.0.co;2-3
• 作为产物：
  描述：

  3-甲基-3-丁烯-1-醇 、 3-溴丙烯 在 正丁基锂 、 potassium hydride 作用下， 以 正己烷 为溶剂， 以28%的产率得到3-methylene-6-hepten-1-ol
  参考文献：
  名称：

  Synthesis of a Butyrolactone Precursor of an Algae Nonaether from an Enantiopure Glycol Obtained by Hoppe's Chemistry

  摘要：

  Homoallyl carbamate 20, (-)-sparteine, and sBuLi gave a lithium derivative which was formylated with DMF giving the crude aldehydocarbamate 19. With Lithium aluminum hydride in refluxing THF, this compound provided diol 22 in 90% overall yield and with 96% ee. This material was carried on to the gamma-lactone monoethers 13 (benzyl ether) or 14 (trityl ether). These compounds should be precursors for synthesizing the naturally occurring nonaether 7.

  DOI：

  10.1002/(sici)1099-0690(199806)1998:6<1023::aid-ejoc1023>3.0.co;2-3

文献信息

• Asymmetric Synthesis of Chiral Cyclopentanes Bearing an All-Carbon Quaternary Stereocenter by Zirconium-Catalyzed Double Carboalumination
  作者：Shiqing Xu、Chuan Wang、Masato Komiyama、Yasuhiko Tomonari、Ei-ichi Negishi

  DOI：10.1002/anie.201706198

  日期：2017.9.11

  All-carbon quaternary stereocenters: A zirconium-catalyzed double carboalumination of various unactivated 1,5-dienes provides efficient access to chiral cyclopentanes with two stereocenters, including one all-carbon quaternary stereocenter, through the formation of two new C−C bonds as well as one C−Al bond with high diastereo- and enantioselectivity.

  全碳四元立体中心：各种未活化的1,5-二烯经锆催化的双碳铝键合可通过形成两个新的C-C键，有效地利用两个立体中心（包括一个全碳四元立体中心）有效地接触手性环戊烷作为具有高非对映选择性和对映选择性的C-Al键。
• Studies on the Alkylation of 3-Methyl-3-buten-1-ol Dianion:  An Efficient Synthesis of 3-Methylene-1-alkanols Including a San Jose Scale Sex Pheromone
  作者：Kelvin H. Yong、John A. Lotoski、J. Michael Chong

  DOI：10.1021/jo015940w

  日期：2001.11.1
• Synthesis of a Butyrolactone Precursor of an Algae Nonaether from an Enantiopure Glycol Obtained by Hoppe's Chemistry
  作者：Markus Menges、Reinhard Brückner

  DOI：10.1002/(sici)1099-0690(199806)1998:6<1023::aid-ejoc1023>3.0.co;2-3

  日期：1998.6

  Homoallyl carbamate 20, (-)-sparteine, and sBuLi gave a lithium derivative which was formylated with DMF giving the crude aldehydocarbamate 19. With Lithium aluminum hydride in refluxing THF, this compound provided diol 22 in 90% overall yield and with 96% ee. This material was carried on to the gamma-lactone monoethers 13 (benzyl ether) or 14 (trityl ether). These compounds should be precursors for synthesizing the naturally occurring nonaether 7.