(6R,7S)-7-amino-7,8-dihydro-α-bisabolene | 105281-43-4

• 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: (6R,7S)-7-amino-7,8-dihydro-α-bisabolene
• 英文别名: (2S)-6-methyl-2-[(1R)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-amine
• CAS: 105281-43-4
• 化学式: C₁₅H₂₇N
• 分子量: 221.386
• InChiKey: QZQOMRYLDNFLCE-GJZGRUSLSA-N

物化性质

• 沸点：
  303.7±11.0 °C(Predicted)
• 密度：
  0.895±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (6R,7S)-7-amino-7,8-dihydro-α-bisabolene 在 potassium carbonate 、 碘甲烷 作用下， 以 丙酮 为溶剂， 反应 8.0h， 以32%的产率得到(+)-R-E-α-bisabolene
  参考文献：
  名称：

  (6R,7S)-7-amino-7,8-dihydro-.alpha.-bisabolene, an antimicrobial metabolite from the marine sponge Halichondria sp

  摘要：

  DOI：

  10.1021/jo00376a014
• 作为产物：
  描述：

  2-Methyl-propane-2-sulfinic acid [1-methoxy-5-methyl-hex-5-en-(E)-ylidene]-amide 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 盐酸 、 cerium(III) chloride 、 氰化钠 、 叔丁基锂 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 甲苯 、 正戊烷 为溶剂， 反应 48.0h， 生成 (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

文献信息

• Structure–activity of antifungal compounds inspired by aminobisabolenes from the sponge Halichondria sp.
  作者：Matthew T. Jamison、Jocelyn Macho、Tadeusz F. Molinski

  DOI：10.1016/j.bmcl.2016.09.053

  日期：2016.11

  Structure-activity relationships of the antifungal aminobisabolene natural product, 1 isolated from Halichondria sp., and synthetic analogs were explored, in parallel with the antidermatophytic allylamine, Terbinafine (R), against a panel of pathogenic fungi: Candida spp., Cuptococcus spp. and Trichophyton rubrum. Interpretation of the results suggest different modes of action in antifungal activity for the two classes of compounds. (C) 2016 Elsevier Ltd. All rights reserved.
• 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.
• (6R,7S)-7-amino-7,8-dihydro-.alpha.-bisabolene, an antimicrobial metabolite from the marine sponge Halichondria sp
  作者：Brian W. Sullivan、D. John Faulkner、Kelvin T. Okamoto、Marie H. M. Chen、Jon Clardy

  DOI：10.1021/jo00376a014

  日期：1986.12