tricalysiolide B | 877670-72-9

• 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: tricalysiolide B
• 英文别名: (1S,4S,9R,12S,13R,16R,17R)-9,17-dihydroxy-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.01,13.04,12.05,9]nonadec-5-en-7-one
• CAS: 877670-72-9
• 化学式: C₂₀H₂₈O₅
• 分子量: 348.439
• InChiKey: RMWYNGTXQIWPHK-BIVJBNGQSA-N

物化性质

• 熔点：
  236-239 °C
• 沸点：
  593.4±50.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tricalysiolide B 在 吡啶 、 sodium tetrahydroborate 、 sodium carbonate 作用下， 以 乙醇 为溶剂， 反应 66.08h， 生成 (1S,4S,9R,12S,13R,16R,17R)-12-methylspiro[8-oxapentacyclo[14.2.1.01,13.04,12.05,9]nonadec-5-ene-17,2'-oxirane]-7-one
  参考文献：
  名称：

  Tricalysiolides A–F, new rearranged ent-kaurane diterpenes from Tricalysia dubia

  摘要：

  Six rearranged ent-kaurane diterpenes, tricalysiolides A-F, having the cafestol-type carbon framework were isolated from the wood of Tricalysia dubia (Rubiaceae). Their absolute structures were determined on the basis of the 2D NMR spectroscopy, X-ray crystallographic analysis, and chemical methods. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.024
• 作为产物：
  描述：

  cafestol diacetate 在 sodium chlorite 、 sodium dihydrogenphosphate dihydrate 、 2-甲基-2-丁烯 、 (2R,2′R)-(+)-[N,N′-bis(2-pyridylmethyl)]-2,2′-bipyrrolidinebis(acetonitrile)iron(II) hexafluoroantimonate 、 双氧水 、 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 5.5h， 生成 tricalysiolide B
  参考文献：
  名称：

  Cafestol to Tricalysiolide B and Oxidized Analogues: Biosynthetic and Derivatization Studies Using Non-heme Iron Catalyst Fe(PDP)

  摘要：

  The tricalysiolides are a recently isolated class of diterpene natural products featuring the carbon backbone of the wellknown coffee extract, cafestol. Herein we validate the use of our non-heme iron complex, Fe(PDP), as an oxidative tailoring enzyme mimic to test the proposal that this class of natural products derives from cafestol via cytochrome P-450-mediated furan oxidation. Thereafter, as predicted by computational analysis, C-H oxidation derivatization studies provided a novel 2 degrees alcohol product as a single diastereomer.

  DOI：

  10.1055/s-0032-1317708

文献信息

• Tricalysiamides A−D, Diterpenoid Alkaloids from <i>Tricalysia dubia</i>
  作者：Koichi Nishimura、Yukio Hitotsuyanagi、Noriko Sugeta、Haruhiko Fukaya、Yutaka Aoyagi、Tomoyo Hasuda、Takeshi Kinoshita、Koichi Takeya

  DOI：10.1021/np0680681

  日期：2007.5.25

  Four rearranged ent-kaurane diterpenoid alkaloids, tricalysiamides A-D (1-4), having a cafestol-type carbon framework were isolated from the wood of Tricalysia dubia. Their absolute structures were determined on the basis of 2D NMR spectroscopy, X-ray crystallographic analysis, and chemical methods.
• Tricalysiolides A–F, new rearranged ent-kaurane diterpenes from Tricalysia dubia
  作者：Koichi Nishimura、Yukio Hitotsuyanagi、Noriko Sugeta、Kei-ichi Sakakura、Kazuya Fujita、Haruhiko Fukaya、Yutaka Aoyagi、Tomoyo Hasuda、Takeshi Kinoshita、Dong-Hui He、Hideaki Otsuka、Yoshio Takeda、Koichi Takeya

  DOI：10.1016/j.tet.2005.11.024

  日期：2006.2

  Six rearranged ent-kaurane diterpenes, tricalysiolides A-F, having the cafestol-type carbon framework were isolated from the wood of Tricalysia dubia (Rubiaceae). Their absolute structures were determined on the basis of the 2D NMR spectroscopy, X-ray crystallographic analysis, and chemical methods. (c) 2005 Elsevier Ltd. All rights reserved.
• Cafestol to Tricalysiolide B and Oxidized Analogues: Biosynthetic and Derivatization Studies Using Non-heme Iron Catalyst Fe(PDP)
  作者：K. Houk、M. White、Marinus Bigi、Peng Liu、Lufeng Zou

  DOI：10.1055/s-0032-1317708

  日期：——

  The tricalysiolides are a recently isolated class of diterpene natural products featuring the carbon backbone of the wellknown coffee extract, cafestol. Herein we validate the use of our non-heme iron complex, Fe(PDP), as an oxidative tailoring enzyme mimic to test the proposal that this class of natural products derives from cafestol via cytochrome P-450-mediated furan oxidation. Thereafter, as predicted by computational analysis, C-H oxidation derivatization studies provided a novel 2 degrees alcohol product as a single diastereomer.