(2R)-1,2-O-cyclohexylidene-1,2-dihydroxytetradecan-3-one | 1024006-16-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-1,2-O-cyclohexylidene-1,2-dihydroxytetradecan-3-one
• 英文别名: 1-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]dodecan-1-one
• CAS: 1024006-16-3
• 化学式: C₂₀H₃₆O₃
• 分子量: 324.504
• InChiKey: XFOUPGKDQHDLDG-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R)-1,2-O-cyclohexylidene-1,2-dihydroxytetradecan-3-one 、 3-溴丙烯 在 三氯化铁 、 锌 作用下， 反应 0.67h， 生成 (2R,3S)-1,2-O-cyclohexylidene-3-undecylhex-5-ene-1,2,3-triol 、 (2R,3R)-1,2-O-cyclohexylidene-3-undecylhex-5-ene-1,2,3-triol
  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：

  在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以6.86 g的产率得到(2R)-1,2-O-cyclohexylidene-1,2-dihydroxytetradecan-3-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

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.