(3aα,4β,6aα)-1,3-dibenzylhexahydro-4-(3-methoxypropyl)-1H-thieno<3,4-d>imidazol-2(3H)-one | 288392-52-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并咪唑类化合物
• 英文名称: (3aα,4β,6aα)-1,3-dibenzylhexahydro-4-(3-methoxypropyl)-1H-thieno<3,4-d>imidazol-2(3H)-one
• 英文别名: (3aS,4S,6aR)-1,3-Dibenzyl-4-(3-methoxy-propyl)-tetrahydro-1H-thieno<3,4-d>imidazol-2(3H)-on；(3aS)-1,3-dibenzyl-4t-(3-methoxy-propyl)-(3ar,6ac)-tetrahydro-thieno[3,4-d]imidazol-2-one；(3aS,4S,6aR)-1,3-dibenzyl-4-(3-methoxypropyl)-3a,4,6,6a-tetrahydrothieno[3,4-d]imidazol-2-one
• CAS: 288392-52-9
• 化学式: C₂₃H₂₈N₂O₂S
• 分子量: 396.554
• InChiKey: UBZGJYPBSVGCSL-FKBYEOEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  58.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (3AS-cis)-1,3-dibenzyltetrahydro-4-(3-methoxypropylidene)-1H-thieno(3,4-d)imidazol-2(3H)-one 在 氢气 、 sodium acetate 、 palladium(II) hydroxide 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、500.01 kPa 条件下， 以93.6%的产率得到(3aα,4β,6aα)-1,3-dibenzylhexahydro-4-(3-methoxypropyl)-1H-thieno<3,4-d>imidazol-2(3H)-one
  参考文献：
  名称：

  [EN] A PROCESS FOR PRODUCING D-BIOTIN INTERMEDIATES
  [FR] PROCÉDÉ DE PRODUCTION D'INTERMÉDIAIRES DE D-BIOTINE

  摘要：

  The present invention provides a process for producing a biotin intermediate compound of formula (I), or a geometrical isomer thereof or a geometrical isomeric mixture thereof in the presence of a catalyst, wherein R1 and R1' are independently H, lower alkyl, aryl or acyl group, optionally substituted by one or more substituents; and R2 is lower alkyl optionally substituted by lower alkoxyl or carboxyl group. According to the present invention, the process surprisingly reduces the reaction pressure while maintaining high yield and selectivity in industrial scale, and thus saves investment on facility and increases safety in industry.

  公开号：

  WO2021224295A1

文献信息

• Diarylcuprates for Selective Syntheses of Multifunctionalized Ketones from Thioesters under Mild Conditions
  作者：Daiki Kato、Tomoya Murase、Jalindar Talode、Haruki Nagae、Hayato Tsurugi、Masahiko Seki、Kazushi Mashima

  DOI：10.1002/chem.202200474

  日期：2022.5.6

  copper-mediated ketone synthesis could be applied to the synthesis of not only gluconolactone-derived ketone 6, a synthetic intermediate in the transformation to the SGLT2 inhibitor canagliflozin, but also thiolactol 8, a valuable synthetic intermediate for (+)-biotin. Control experiments on an isolated diphenylcuprate(I), [CuPh2 ]- (12), and DFT calculations revealed that this ketone synthesis proceeded

  通过使用在环境温度下以 1:1.3-1.5 的比例从铜 (I) 盐和芳基格氏试剂原位生成的二芳基铜酸盐 (I) 从硫酯选择性地合成酮。在酮合成过程中，各种官能团，如羰基（酮、酯和酰胺）、O-保护基、卤素和杂芳烃，都可以以优异的收率得到多官能化酮。这种铜介导的酮合成不仅可用于合成葡萄糖酸内酯衍生的酮 6（一种转化为 SGLT2 抑制剂卡格列净的合成中间体），还可以用于合成硫代乳酸 8（一种有价值的 (+)-生物素合成中间体）。对分离的二苯铜酸盐 (I)、[CuPh2]- (12) 的对照实验，
• Versuche zur Biotinsynthese. Herstellung von (3aS, 6aR)-1, 3-Dibenzyl-tetrahydro-4H-thieno[3, 4-d]imidazol-2,4(1H)-dion
  作者：M. Gerecke、J.-P. Zimmermann、W. Aschwanden

  DOI：10.1002/hlca.19700530514

  日期：——

  AbstractA modification of the biotin synthesis of Goldberg & Sternbach is described, enantiomers being separated in the first steps and wrong isomers recyclised. The conversion of the lactone 15 to the thiolactone 16 is done by a new method using potassium thioacetate in high boiling solvents.
• WO2022/260168
  申请人：——

  公开号：——

  公开（公告）日：——