2,2-Dibenzyl-4-(hydroxymethyl)-1,3-dioxolane | 133885-12-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-Dibenzyl-4-(hydroxymethyl)-1,3-dioxolane
• 英文别名: (2,2-dibenzyl-[1,3]dioxolan-4-yl)methanol；(2,2-Dibenzyl-1,3-dioxolan-4-yl)methanol
• CAS: 133885-12-8
• 化学式: C₁₈H₂₀O₃
• 分子量: 284.355
• InChiKey: JBTIJIFMSJEZAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-Dibenzyl-4-(hydroxymethyl)-1,3-dioxolane 在 三氟甲磺酸三甲基硅酯 、 dimethyl sulfide borane 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 3-(Benzyloxy)-2-(dibenzylmethoxy)-1-propanol
  参考文献：
  名称：

  A selectivity study of activated ketal reduction with borane dimethyl sulfide

  摘要：

  A chemo- and regioselectivity study of the reagent combination BH3.SMe2/TMSOTf for ketal reduction has been undertaken. It has revealed that simple 1,3-dioxanes reduce cleanly at low temperature in CH2Cl2 while simple 1,3-dioxolanes may give complete ring cleavage and dimerization products. A study of reduction of 4-substituted 1,3-dioxolanes has revealed a solvent-directed regioselectivity which in THF favors the secondary protected derivative. A mechanism is postulated to account for the selectivities based on recent thinking on acetal substitution reactions.

  DOI：

  10.1021/jo00076a041
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以1.57 g的产率得到2,2-Dibenzyl-4-(hydroxymethyl)-1,3-dioxolane
  参考文献：
  名称：

  Organocatalytic kinetic resolution of racemic primary alcohols using a chiral 1,2-diamine derived from (S)-proline

  摘要：

  A highly efficient and good enantioselective organocatalytic asymmetric acylation of racemic primary alcohols with acyl chlorides has been achieved catalyzed by a chiral 1,2-diamine derived from (S)-proline. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.034

文献信息

• Reduction of activated ketals with borane-dimethyl sulphide
  作者：Roger Hunter、Birgit Bartels、Joseph P. Michael

  DOI：10.1016/s0040-4039(00)74497-2

  日期：1991.2

  Borane-Dimethyl sulphide reduces ketals activated with TMSOTf at -78-degrees-C in dichloromethane. The scope and selectivity of the reagent has been investigated.
• Terao, Yoshiyasu; Tsuji, Keiichiro; Murata, Masakazu, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 6, p. 1653 - 1655
  作者：Terao, Yoshiyasu、Tsuji, Keiichiro、Murata, Masakazu、Achiwa, Kazuo、Nishio, Toshiyuki、et al.

  DOI：——

  日期：——
• Bartels Birgit, Hunter Roger, J. Org. Chem, 58 (1993) N 24, S 6756-6765
  作者：Bartels Birgit, Hunter Roger

  DOI：——

  日期：——
• US5312950A
  申请人：——

  公开号：US5312950A

  公开（公告）日：1994-05-17