(3S,6R)-6-acetoxy-3-(N-1-naphthyl)carbamoyloxy-2,6-dimethyloct-7-en-2-ol | 252857-34-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (3S,6R)-6-acetoxy-3-(N-1-naphthyl)carbamoyloxy-2,6-dimethyloct-7-en-2-ol
• 英文别名: [(3R,6S)-7-hydroxy-3,7-dimethyl-6-(naphthalen-1-ylcarbamoyloxy)oct-1-en-3-yl] acetate
• CAS: 252857-34-4
• 化学式: C₂₃H₂₉NO₅
• 分子量: 399.487
• InChiKey: SPEZHRLXGDSTNO-REWPJTCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,6R)-6-acetoxy-3-(N-1-naphthyl)carbamoyloxy-2,6-dimethyloct-7-en-2-ol 在 吡啶 、 甲醇 、 三苯基氢化锡 、 sodium methylate 、 4-甲基苯磺酸吡啶 、 三氯氧磷 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 59.5h， 生成 2H-吡喃-3-醇,6-乙烯基四氢-2,2,6-三甲基-,(3S,6R)-
  参考文献：
  名称：

  Enantioselective synthesis of each stereoisomer of the pyranoid linalool oxides: the linalool route

  摘要：

  Each of the four enantiomerically pure tetrahydropyran linalool oxides was prepared by separate enantioselective Sharpless dihydroxylation of (R)- or (S)-linalyl acetate with AD-mix-alpha or AD-mix-beta, followed by a completely stereoselective N-phenylselenophthalimide cyclization of an intermediate allylic alcohol. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00359-6
• 作为产物：
  描述：

  1-Alapha-萘异氰酸酯 、 (3S/R,6R)-6-acetoxy-2,6-dimethyloct-7-en-2,3-diol 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以70%的产率得到(3S,6R)-6-acetoxy-3-(N-1-naphthyl)carbamoyloxy-2,6-dimethyloct-7-en-2-ol
  参考文献：
  名称：

  Enantioselective synthesis of each stereoisomer of the pyranoid linalool oxides: the linalool route

  摘要：

  Each of the four enantiomerically pure tetrahydropyran linalool oxides was prepared by separate enantioselective Sharpless dihydroxylation of (R)- or (S)-linalyl acetate with AD-mix-alpha or AD-mix-beta, followed by a completely stereoselective N-phenylselenophthalimide cyclization of an intermediate allylic alcohol. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00359-6

文献信息

• Enantioselective synthesis of each stereoisomer of the pyranoid linalool oxides: the linalool route
  作者：Giovanni Vidari、Anna Di Rosa、Giuseppe Zanoni、Carlo Bicchi

  DOI：10.1016/s0957-4166(99)00359-6

  日期：1999.9

  Each of the four enantiomerically pure tetrahydropyran linalool oxides was prepared by separate enantioselective Sharpless dihydroxylation of (R)- or (S)-linalyl acetate with AD-mix-alpha or AD-mix-beta, followed by a completely stereoselective N-phenylselenophthalimide cyclization of an intermediate allylic alcohol. (C) 1999 Elsevier Science Ltd. All rights reserved.