neomacrophorin I | 1558036-24-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: neomacrophorin I
• 英文别名: [(1R,6S)-6-[[(1S,4aR,6R,8aR)-6-hydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]methyl (2R,3S)-2,3-dihydroxybutanoate
• CAS: 1558036-24-0
• 化学式: C₂₆H₃₆O₈
• 分子量: 476.567
• InChiKey: WTPCVDMJSKOJKE-VXJMVHJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  neomacrophorin I 、 苯甲酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.67h， 以3 mg的产率得到
  参考文献：
  名称：

  Neomacrophorin I, II, and III, novel drimenyl cyclohexanes with hydroxylated butanoates from Trichoderma sp. 1212-03

  摘要：

  Neomacrophorins I(1), II(2), and III (3) were isolated from the culture broth of Trichoderma sp. 1212-03, which was collected at Shirakami Mountainous area in Japan. Structural analyses disclosed that these resemble known macrophorins but possess axial-hydroxy group at C3 as well as different side chains at C7'. These are diastereomeric forms of macrophorins for 5',6'-epoxide functionality. The NMR analyses suggested their relative configurational relationship between the C1-C15 drimene and C1'-C7' epoxyquinone moieties. ECD spectral discussions verified them particularly for C5',C6'-epoxyquinone (1), C5',C6'-epoxysemiquinone (2 and 3), and 2",3"-dihydroxybutanoate moiety in 1 and 2. The configuration of C3"-stereocenter of 3 was determined by chiral GC MS after converting into methyl (S)-3"-hydroxybutanoate by basic of 3 methanolysis. Biological assays disclosed that 1 induces hyphal branching of Cochliobolus miyabeanus as well as cytotoxicity against human colorectal cancer COLO 201. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.087