(S)-(+)-chelonin B | 133985-27-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-(+)-chelonin B
• 英文别名: Chelonin B；(1S)-1-(3-bromo-4-methoxyphenyl)-2-[2-(1H-indol-3-yl)ethylamino]ethanol
• CAS: 133985-27-0
• 化学式: C₁₉H₂₁BrN₂O₂
• 分子量: 389.292
• InChiKey: WVUGPBDGSNGOCB-GOSISDBHSA-N

物化性质

• 熔点：
  260 °C (decomp)
• 沸点：
  581.3±50.0 °C(Predicted)
• 密度：
  1.412±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  57.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (S)-(+)-chelonin B 在 吡啶 作用下， 反应 21.0h， 以84%的产率得到Chelonin B N,O-diacetate
  参考文献：
  名称：

  Aromatic alkaloids from the marine sponge Chelonaplysilla sp

  摘要：

  Four novel alkaloids derived from tryptophan and tyrosine subunits have been isolated from the marine sponge Chelonaplysilla sp. collected from a marine lake in Palau. The structures of chelonin A (3), chelonin B (4), bromochelonin B (5), and chelonin C (6) were determined by interpretation of spectral data and chemical conversions. Chelonin A (3) and C (6) are the first natural products incorporating a 2,6-disubstituted morpholine ring. Chelonin A (3), chelonin B (4), and bromochelonin B (5) exhibited antimicrobial activity against Bacillus subtilis, while chelonin A (3) showed in vivo antiinflammatory activity.

  DOI：

  10.1021/jo00014a015
• 作为产物：
  描述：

  2-bromo-1-methoxy-4-vinylbenzene 在 原乙酸三甲酯 、 4-二甲氨基吡啶 、 potassium osmate(VI) 、 三甲基氯硅烷 、 Hydroquinone 1,4-phthalazinediyl diether 、 dimethyl sulfide borane 、 potassium phtalimide 、 一水合肼 、 N,N'-二环己基碳二亚胺 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 、 叔丁醇 为溶剂， 反应 52.86h， 生成 (S)-(+)-chelonin B
  参考文献：
  名称：

  The asymmetric synthesis and stereochemical assignment of chelonin B

  摘要：

  The first total synthesis of the marine natural product (S)-(+)-chelonin B is described. The key reactions employed include Sharpless asymmetric dihydroxylation of a styrene derivative, catalytic ring-opening of an epoxide and sequential deprotection-rearrangement of a phthalimido indole acetate. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01555-6

文献信息

• BOBZIN, STEVEN C.;FAULKNER, D. JOHN, J. ORG. CHEM., 56,(1991) N4, C. 4403-4407
  作者：BOBZIN, STEVEN C.、FAULKNER, D. JOHN

  DOI：——

  日期：——
• The asymmetric synthesis and stereochemical assignment of chelonin B
  作者：Nicholas J Lawrence、Simon M Bushell

  DOI：10.1016/s0040-4039(01)01555-6

  日期：2001.10

  The first total synthesis of the marine natural product (S)-(+)-chelonin B is described. The key reactions employed include Sharpless asymmetric dihydroxylation of a styrene derivative, catalytic ring-opening of an epoxide and sequential deprotection-rearrangement of a phthalimido indole acetate. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Aromatic alkaloids from the marine sponge Chelonaplysilla sp
  作者：Steven C. Bobzin、D. John Faulkner

  DOI：10.1021/jo00014a015

  日期：1991.7

  Four novel alkaloids derived from tryptophan and tyrosine subunits have been isolated from the marine sponge Chelonaplysilla sp. collected from a marine lake in Palau. The structures of chelonin A (3), chelonin B (4), bromochelonin B (5), and chelonin C (6) were determined by interpretation of spectral data and chemical conversions. Chelonin A (3) and C (6) are the first natural products incorporating a 2,6-disubstituted morpholine ring. Chelonin A (3), chelonin B (4), and bromochelonin B (5) exhibited antimicrobial activity against Bacillus subtilis, while chelonin A (3) showed in vivo antiinflammatory activity.