2-Methyl-propane-2-sulfinic acid [(S)-1,5-dimethyl-1-((R)-4-methyl-cyclohex-3-enyl)-hex-4-enyl]-amide | 1026584-40-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-Methyl-propane-2-sulfinic acid [(S)-1,5-dimethyl-1-((R)-4-methyl-cyclohex-3-enyl)-hex-4-enyl]-amide
• 英文别名: (R)-2-methyl-N-[(2S)-6-methyl-2-[(1R)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-yl]propane-2-sulfinamide
• CAS: 1026584-40-6
• 化学式: C₁₉H₃₅NOS
• 分子量: 325.559
• InChiKey: ZFCGZIOOIDEDIV-LQBOVUBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  48.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Methyl-propane-2-sulfinic acid [(S)-1,5-dimethyl-1-((R)-4-methyl-cyclohex-3-enyl)-hex-4-enyl]-amide 在 盐酸 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 2.0h， 以87%的产率得到(6R,7S)-7-amino-7,8-dihydro-α-bisabolene
  参考文献：
  名称：

  Asymmetric α-Alkylation of N‘-tert-Butanesulfinyl Amidines. Application to the Total Synthesis of (6R,7S)-7-Amino-7,8-dihydro-α-bisabolene

  摘要：

  A highly diastereoselective alpha-alkylation of N'-tert-butanesulfinyl amidines has been developed along with methods for converting the alkylation products to enantiomerically enriched amines that incorporate both alpha- and beta-stereocenters. The utility of this chemistry is further demonstrated by the first asymmetric synthesis of the antimicrobial marine natural product (6R,7S)-7-amino-7,8-dihydro-alpha-bisabolene.

  DOI：

  10.1021/ja044753n
• 作为产物：
  描述：

  (NE,R)-2-methyl-N-[(2R)-5-methyl-1-morpholin-4-yl-2-prop-2-enylhex-5-enylidene]propane-2-sulfinamide 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 cerium(III) chloride 、 叔丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 甲苯 、 正戊烷 为溶剂， 反应 5.0h， 生成 2-Methyl-propane-2-sulfinic acid [(S)-1,5-dimethyl-1-((R)-4-methyl-cyclohex-3-enyl)-hex-4-enyl]-amide
  参考文献：
  名称：

  Asymmetric α-Alkylation of N‘-tert-Butanesulfinyl Amidines. Application to the Total Synthesis of (6R,7S)-7-Amino-7,8-dihydro-α-bisabolene

  摘要：

  A highly diastereoselective alpha-alkylation of N'-tert-butanesulfinyl amidines has been developed along with methods for converting the alkylation products to enantiomerically enriched amines that incorporate both alpha- and beta-stereocenters. The utility of this chemistry is further demonstrated by the first asymmetric synthesis of the antimicrobial marine natural product (6R,7S)-7-amino-7,8-dihydro-alpha-bisabolene.

  DOI：

  10.1021/ja044753n

文献信息

• Asymmetric α-Alkylation of <i>N</i><i>‘</i>-<i>tert</i>-Butanesulfinyl Amidines. Application to the Total Synthesis of (6<i>R</i>,7<i>S</i>)-7-Amino-7,8-dihydro-α-bisabolene
  作者：Takuya Kochi、Jonathan A. Ellman

  DOI：10.1021/ja044753n

  日期：2004.12.1

  A highly diastereoselective alpha-alkylation of N'-tert-butanesulfinyl amidines has been developed along with methods for converting the alkylation products to enantiomerically enriched amines that incorporate both alpha- and beta-stereocenters. The utility of this chemistry is further demonstrated by the first asymmetric synthesis of the antimicrobial marine natural product (6R,7S)-7-amino-7,8-dihydro-alpha-bisabolene.