(3aR,7aS)-2,2-dimethyl-4-phenyl-3a,7a-dihydro-1,3-benzodioxole | 138608-61-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,7aS)-2,2-dimethyl-4-phenyl-3a,7a-dihydro-1,3-benzodioxole
• CAS: 138608-61-4
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: SZUYPBVTERFWQD-UONOGXRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3aR,7aS)-2,2-dimethyl-4-phenyl-3a,7a-dihydro-1,3-benzodioxole 在 biphenyl dioxygenase of Sphingomonas yaniokuyae B₈/36 、 氧气 作用下， 生成 (3aR,7aS,3'aR,7'aS)-2,2,2',2'-Tetramethyl-3a,7a,3'a,7'a-tetrahydro-[4,4']bi[benzo[1,3]dioxolyl]
  参考文献：
  名称：

  Dioxygenase-catalysed dihydroxylation of arene cis-dihydrodiols and acetonide derivatives: a new approach to the synthesis of enantiopure tetraoxygenated bioproducts from arenes

  摘要：

  已鉴定出蒽和苯[a]蒽的顺式二氢二醇，以及苯、氟苯、联苯和菲的顺式二氢二醇的醋酰衍生物，作为双氧酶的底物，分别产生对应的对映体纯烯烃生物产物、双（顺式二氢二醇）和顺式二醇醋酰衍生物。

  DOI：

  10.1039/b612191h
• 作为产物：
  描述：

  (3aS,7aS)-2,2-dimethyl-7,7a-dihydrobenzo[d][1,3]dioxol-4-(3aH)-one 在 吡啶 、 氯化亚砜 、 lithium carbonate 、 lithium chloride 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3aR,7aS)-2,2-dimethyl-4-phenyl-3a,7a-dihydro-1,3-benzodioxole
  参考文献：
  名称：

  Chemical synthesis of optically active cis-cyclohexa-3,5-diene-1,2-diols and their 5-2H-derivatives

  摘要：

  A variety of optically active 3-substituted cis-cyclohexane-3,5-dien-1,2-diol acetonides were readily prepared from chiral 5-(tert-butyldimethylsilyloxy)-2-cyclohexenone through a seven-step reaction in good overall yield. The synthesis also allowed preparation of the acetonide having an H-2-atom at the 5-position. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01014-0

文献信息

• Dioxygenase-catalysed dihydroxylation of arene cis-dihydrodiols and acetonide derivatives: a new approach to the synthesis of enantiopure tetraoxygenated bioproducts from arenes
  作者：Derek R. Boyd、Narain D. Sharma、Tayeb Belhocine、John F. Malone、Stuart McGregor、Christopher C. R. Allen

  DOI：10.1039/b612191h

  日期：——

  cis-Dihydrodiols of anthracene and benz[a]anthracene, and acetonide derivatives of the cis-dihydrodiols of benzene, fluorobenzene, biphenyl and phenanthrene have been identified as substrates for dioxygenase enzymes, yielding the corresponding enantiopure arene bioproducts, bis(cis-dihydrodiol)s and cis-diol acetonides respectively.

  已鉴定出蒽和苯[a]蒽的顺式二氢二醇，以及苯、氟苯、联苯和菲的顺式二氢二醇的醋酰衍生物，作为双氧酶的底物，分别产生对应的对映体纯烯烃生物产物、双（顺式二氢二醇）和顺式二醇醋酰衍生物。
• Chemical synthesis of optically active cis-cyclohexa-3,5-diene-1,2-diols and their 5-2H-derivatives
  作者：Takeshi Hanazawa、Sentaro Okamoto、Fumie Sato

  DOI：10.1016/s0040-4039(01)01014-0

  日期：2001.8

  A variety of optically active 3-substituted cis-cyclohexane-3,5-dien-1,2-diol acetonides were readily prepared from chiral 5-(tert-butyldimethylsilyloxy)-2-cyclohexenone through a seven-step reaction in good overall yield. The synthesis also allowed preparation of the acetonide having an H-2-atom at the 5-position. (C) 2001 Elsevier Science Ltd. All rights reserved.