(5R)-5-[(2R)-1,2-dihydroxyethyl]-5-hexadecanolide | 1024006-22-1

• 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: (5R)-5-[(2R)-1,2-dihydroxyethyl]-5-hexadecanolide
• 英文别名: (6R)-6-[(1R)-1,2-dihydroxyethyl]-6-undecyloxan-2-one
• CAS: 1024006-22-1
• 化学式: C₁₈H₃₄O₄
• 分子量: 314.466
• InChiKey: HDFFGYVACNSCHQ-SJLPKXTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5R)-5-[(2R)-1,2-dihydroxyethyl]-5-hexadecanolide 在 sodium periodate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以135 mg的产率得到(2R)-6-oxo-2-undecyloxane-2-carbaldehyde
  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：

  (6R)-6-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]-6-undecyloxan-2-one 在 水 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以71.7%的产率得到(5R)-5-[(2R)-1,2-dihydroxyethyl]-5-hexadecanolide
  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.