(R)-1-chloronon-8-en-2-ol | 915314-56-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: (R)-1-chloronon-8-en-2-ol
• CAS: 915314-56-6
• 化学式: C₉H₁₇ClO
• 分子量: 176.686
• InChiKey: KVBNOAPCUOXMFV-SECBINFHSA-N

物化性质

• 沸点：
  260.2±33.0 °C(Predicted)
• 密度：
  0.973±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  11.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  (R)-1-chloronon-8-en-2-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 2,6-二甲基吡啶 、 乙酰氯 、 间氯过氧苯甲酸 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正庚烷 、 二氯甲烷 、 乙基苯 、 丙酮 为溶剂， 反应 91.83h， 生成 3,3'-[(2R,15R)-2,5-dihydroxyhexadec-8(E)-ene-1,16-diyl]bis[(S)-5-methyl-5H-furan-2-one]
  参考文献：
  名称：

  Total Synthesis of (+)-cis-Sylvaticin:  Double Oxidative Cyclization Reactions Catalyzed by Osmium

  摘要：

  The double oxidative cyclization of dienes is a viable procedure for making complex natural products containing cis-THF units. A double deprotection/double oxidative cyclization strategy using catalytic osmium tetroxide was used to construct the bisheterocyclic core of cis-sylvaticin and ultimately confirm its structure. The natural product was then prepared by a short sequence of reactions that is exceptionally concise: the final route being just 13 linear steps and 19 chemical operations in total.

  DOI：

  10.1021/ja0660148
• 作为产物：
  描述：

  左旋环氧氯丙烷 、 6-溴-1-己烯 在 magnesium bromide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以51%的产率得到(R)-1-chloronon-8-en-2-ol
  参考文献：
  名称：

  Total Synthesis of (+)-cis-Sylvaticin:  Double Oxidative Cyclization Reactions Catalyzed by Osmium

  摘要：

  The double oxidative cyclization of dienes is a viable procedure for making complex natural products containing cis-THF units. A double deprotection/double oxidative cyclization strategy using catalytic osmium tetroxide was used to construct the bisheterocyclic core of cis-sylvaticin and ultimately confirm its structure. The natural product was then prepared by a short sequence of reactions that is exceptionally concise: the final route being just 13 linear steps and 19 chemical operations in total.

  DOI：

  10.1021/ja0660148

文献信息

• 一种光学活性N-叔丁氧羰基-2-氨基-8-壬烯酸二环己胺盐的合成方法
  申请人：浙江九洲药物科技有限公司

  公开号：CN108689909A

  公开（公告）日：2018-10-23

  本发明提供了一种制备光学活性N‑叔丁氧羰基‑2‑氨基‑8‑壬烯酸二环己胺盐的方法，其中，X为卤素。该方法通过光延反应实现构型反转，能够高收率和高纯度获得光学纯度产品N‑叔丁氧羰基‑2‑氨基‑8‑壬烯酸二环己胺盐。
• Stereoselective Syntheses of Rolliniastatin 1, Rollimembrin, and Membranacin
  作者：Gyochang Keum、Cheol Hee Hwang、Soon Bang Kang、Youseung Kim、Eun Lee

  DOI：10.1021/ja0526867

  日期：2005.7.1

  A radical cyclization of beta-alkoxyvinyl sulfoxides-Pummerer rearrangement-allylation protocol was successfully applied to the synthesis of the threo/cis/threo/cis/erythro bis-oxolane moiety in rolliniastatin 1 (1), rollimembrin (2), and membranacin (3).
• Concise Syntheses of the Natural Products (+)-Sylvaticin and (+)-<i>cis</i>-Sylvaticin
  作者：Timothy J. Donohoe、Robert M. Harris、Oliver Williams、Gráinne C. Hargaden、Jeremy Burrows、Jeremy Parker

  DOI：10.1021/ja9049959

  日期：2009.9.9

  Two concise syntheses of the natural products cis-sylvaticin and sylvaticin are reported, using oxidative cyclization methodology as the key step. A sequential solvolysis/hydride shift/intramolecular reduction cascade was used to establish the trans stereochemistry of one of the THF rings of sylvaticin.