(S)-5-benzyl-2,2-bis-trifluoromethyl[1,3]dioxolan-4-one | 748134-70-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-5-benzyl-2,2-bis-trifluoromethyl[1,3]dioxolan-4-one
• 英文别名: 5-benzyl-2,2-bis(trifluoromethyl)-1,3-dioxolan-4-one；1,3-Dioxolan-4-one, 5-(phenylmethyl)-2,2-bis(trifluoromethyl)-, (5S)-；(5S)-5-benzyl-2,2-bis(trifluoromethyl)-1,3-dioxolan-4-one
• CAS: 748134-70-5
• 化学式: C₁₂H₈F₆O₃
• 分子量: 314.184
• InChiKey: UDSBAALKVHGVPL-QMMMGPOBSA-N

物化性质

• 沸点：
  295.4±35.0 °C(Predicted)
• 密度：
  1.494±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (S)-5-benzyl-2,2-bis-trifluoromethyl[1,3]dioxolan-4-one 在 N-羟基-7-氮杂苯并三氮唑 、 N,N-二异丙基乙胺 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 cyclo-(β-Ala-Hiv-Val-Phlac-Ile)
  参考文献：
  名称：

  A New Strategy for Solid-Phase Depsipeptide Synthesis Using Recoverable Building Blocks

  摘要：

  The technique of choice for synthesis of small-scale depsipeptides is on a solid support. However, if expensive monomers have to be incorporated, solid-phase synthesis can quickly turn out to be unattractive because of its low atom economy. Herein, we describe a new type of recoverable and reuseable alpha-hydroxy acid building block for solid-phase synthesis and its application in the synthesis of a number of small cyclic depsipeptides.

  DOI：

  10.1021/ol047653v
• 作为产物：
  描述：

  L-(-)-3-苯基乳酸 、 六氟丙酮 以 二甲基亚砜 为溶剂， 反应 1.5h， 以88%的产率得到(S)-5-benzyl-2,2-bis-trifluoromethyl[1,3]dioxolan-4-one
  参考文献：
  名称：

  Two Complementary Approaches toward 2-Alkoxy Carboxylic Acid Synthesis from 1,3-Dioxolan-4-ones

  摘要：

  Two complementary approaches to prepare 2-alkoxy carboxylic acids have been developed. Reductive ring opening of various 1,3-dioxolan-4-ones using TiCl4/Et3SiH or (BuMgCl)-Bu-t affords the desired 2-alkoxy carboxylic acid in moderate to excellent chemical yield without loss of optical purity.

  DOI：

  10.1021/jo049784f

文献信息

• Two Complementary Approaches toward 2-Alkoxy Carboxylic Acid Synthesis from 1,3-Dioxolan-4-ones
  作者：Leonard L. Winneroski、Yanping Xu

  DOI：10.1021/jo049784f

  日期：2004.7.1

  Two complementary approaches to prepare 2-alkoxy carboxylic acids have been developed. Reductive ring opening of various 1,3-dioxolan-4-ones using TiCl4/Et3SiH or (BuMgCl)-Bu-t affords the desired 2-alkoxy carboxylic acid in moderate to excellent chemical yield without loss of optical purity.
• A New Strategy for Solid-Phase Depsipeptide Synthesis Using Recoverable Building Blocks
  作者：Fernando Albericio、Klaus Burger、Javier Ruíz-Rodríguez、Jan Spengler

  DOI：10.1021/ol047653v

  日期：2005.2.1

  The technique of choice for synthesis of small-scale depsipeptides is on a solid support. However, if expensive monomers have to be incorporated, solid-phase synthesis can quickly turn out to be unattractive because of its low atom economy. Herein, we describe a new type of recoverable and reuseable alpha-hydroxy acid building block for solid-phase synthesis and its application in the synthesis of a number of small cyclic depsipeptides.