(5R)-5-[(2R)-1,2-O-cyclohexylidene-1,2-dihydroxyethyl]hexadec-2-en-5-olide | 1024006-20-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (5R)-5-[(2R)-1,2-O-cyclohexylidene-1,2-dihydroxyethyl]hexadec-2-en-5-olide
• 英文别名: (2R)-2-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]-2-undecyl-3H-pyran-6-one
• CAS: 1024006-20-9
• 化学式: C₂₄H₄₀O₄
• 分子量: 392.579
• InChiKey: VESJLVJMXMLOSD-FYYLOGMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5R)-5-[(2R)-1,2-O-cyclohexylidene-1,2-dihydroxyethyl]hexadec-2-en-5-olide 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以85%的产率得到(6R)-6-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]-6-undecyloxan-2-one
  参考文献：
  名称：

  Organometallation of (R)-2,3-cyclohexylideneglyceraldehyde derived ketones: a simple and stereoselective strategy for the synthesis of (+)-tanikolide

  摘要：

  Several metal mediated allylations and Grignard additions to ketones 3 and 5, both derived from (R)-2,3-cylcohexylidenegly-ceraldehyde, took place with very high diastereoselectivity producing the same tertiary carbinol 4b as the major product. Subsequently, 4b was exploited to synthesize (+)-tanikolide efficiently through a series of simple reactions employing an RCM strategy. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.034
• 作为产物：
  描述：

  [(4R)-4-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]pentadec-1-en-4-yl] prop-2-enoate 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以94.3%的产率得到(5R)-5-[(2R)-1,2-O-cyclohexylidene-1,2-dihydroxyethyl]hexadec-2-en-5-olide
  参考文献：
  名称：

  Organometallation of (R)-2,3-cyclohexylideneglyceraldehyde derived ketones: a simple and stereoselective strategy for the synthesis of (+)-tanikolide

  摘要：

  Several metal mediated allylations and Grignard additions to ketones 3 and 5, both derived from (R)-2,3-cylcohexylidenegly-ceraldehyde, took place with very high diastereoselectivity producing the same tertiary carbinol 4b as the major product. Subsequently, 4b was exploited to synthesize (+)-tanikolide efficiently through a series of simple reactions employing an RCM strategy. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.034

文献信息

• Organometallation of (R)-2,3-cyclohexylideneglyceraldehyde derived ketones: a simple and stereoselective strategy for the synthesis of (+)-tanikolide
  作者：Prasad Vichare、Angshuman Chattopadhyay

  DOI：10.1016/j.tetasy.2008.01.034

  日期：2008.3

  Several metal mediated allylations and Grignard additions to ketones 3 and 5, both derived from (R)-2,3-cylcohexylidenegly-ceraldehyde, took place with very high diastereoselectivity producing the same tertiary carbinol 4b as the major product. Subsequently, 4b was exploited to synthesize (+)-tanikolide efficiently through a series of simple reactions employing an RCM strategy. (C) 2008 Elsevier Ltd. All rights reserved.