2,3-di-O-allyl-L-ascorbic acid | 88306-61-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 2,3-di-O-allyl-L-ascorbic acid
• 英文别名: 2,3di-(O-allyl)-L-ascorbic acid；(2R)-2-[(1S)-1,2-dihydroxyethyl]-3,4-bis(prop-2-enoxy)-2H-furan-5-one
• CAS: 88306-61-0
• 化学式: C₁₂H₁₆O₆
• 分子量: 256.255
• InChiKey: NCYHJRIUVJRFND-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3-di-O-allyl-L-ascorbic acid 、 6-O-allyl-5-[2,3,4-tri-O-allyl-1-O-(3,3-dimethoxypropyl)-β-D-glucopyranos-6-oxy]-methyl-γ-tocopherol 在 对甲苯磺酸 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 6-O-allyl-5-[2-(5,6-O-methylidene-2,3-di-O-allyl-L-ascorbyl)-ethyl-2,3,4-tri-O-allyl-β-D-glucopyranos-6-oxy]-methyl-γ-tocopherol 、 6-O-allyl-5-[2-(5,6-O-methylidene-2,3-di-O-allyl-L-ascorbyl)-ethyl-2,3,4-tri-O-allyl-β-D-glucopyranos-6-oxy]-methyl-γ-tocopherol
  参考文献：
  名称：

  Transformations of chromanol and tocopherol and synthesis of ascorbate conjugates

  摘要：

  alpha-Tocopherol and as a model compound pentamethylchromanol could be transferred into simple and more complex 5a-ether derivatives including galactopyranose as well as ascorbic acid conjugates. Following elaboration of a glucopyranoside spacer element this could be used for tethering the vitamin E and the vitamin C components to give novel conjugates for subsequent biostudies concerning their proposed synergism of antioxidant properties in tissues. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.066
• 作为产物：
  描述：

  3-溴丙烯 、 维生素 C 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以23%的产率得到2,3-di-O-allyl-L-ascorbic acid
  参考文献：
  名称：

  Transformations of chromanol and tocopherol and synthesis of ascorbate conjugates

  摘要：

  alpha-Tocopherol and as a model compound pentamethylchromanol could be transferred into simple and more complex 5a-ether derivatives including galactopyranose as well as ascorbic acid conjugates. Following elaboration of a glucopyranoside spacer element this could be used for tethering the vitamin E and the vitamin C components to give novel conjugates for subsequent biostudies concerning their proposed synergism of antioxidant properties in tissues. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.066

文献信息

• Ascorbic acid ethers and related compounds
  申请人：ELI LILLY AND COMPANY

  公开号：EP0086554A1

  公开（公告）日：1983-08-24

  Ethers of ascorbic acid, isoascorbic acid, dihydroascorbic acid, dihydroisoascorbic acid, deoxyascorbic acid, and scorbamic acid, and ketals and acetals thereof, having angiogenesis and arthritis inhibiting properties, are provided.

  本研究提供了具有血管生成和关节炎抑制特性的抗坏血酸、异抗坏血酸、二氢抗坏血酸、二氢异抗坏血酸、脱氧抗坏血酸和氨基甲酸的醚及其酮和乙缩醛。
• US4552888A
  申请人：——

  公开号：US4552888A

  公开（公告）日：1985-11-12
• Transformations of chromanol and tocopherol and synthesis of ascorbate conjugates
  作者：Martina Lahmann、Joachim Thiem

  DOI：10.1016/j.tet.2010.12.066

  日期：2011.3

  alpha-Tocopherol and as a model compound pentamethylchromanol could be transferred into simple and more complex 5a-ether derivatives including galactopyranose as well as ascorbic acid conjugates. Following elaboration of a glucopyranoside spacer element this could be used for tethering the vitamin E and the vitamin C components to give novel conjugates for subsequent biostudies concerning their proposed synergism of antioxidant properties in tissues. (C) 2011 Elsevier Ltd. All rights reserved.