5-endo-hydroxy-1,7,7-trimethylbicyclo<2.2.1>heptan-2-one | 107438-74-4

• 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: 5-endo-hydroxy-1,7,7-trimethylbicyclo<2.2.1>heptan-2-one
• 英文别名: (+)-(1R,4R,5S)-5-endo-hydroxycamphor；5-endo-hydroxycamphor；(1R)-5endo-hydroxy-bornan-2-one；(1R)-5endo-Hydroxy-bornan-2-on；5-endo-Hydroxycampher；exo-5-Hydroxy-campher；Rel-(1R,4R,5S)-5-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one；(1R,4R,5S)-5-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
• CAS: 107438-74-4；1126-88-1；1607-84-7；4367-83-3；13948-58-8；22285-79-6
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: DJQYBVLXBVJHMU-BYULHYEWSA-N

物化性质

• 沸点：
  250.9±33.0 °C(predicted)
• 密度：
  1.107±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-endo-hydroxy-1,7,7-trimethylbicyclo<2.2.1>heptan-2-one 在 chromium(VI) oxide 作用下， 以 丙酮 为溶剂， 生成 1,7,7-trimethylbicyclo<2.2.1>heptan-2,5-dione
  参考文献：
  名称：

  Marquet,A. et al., Bulletin de la Societe Chimique de France, 1966, p. 2956 - 2959

  摘要：

  DOI：
• 作为产物：
  描述：

  (1R,4R,5S)-5-endo-hydroxycamphor 5-O-β-D-glucopyranoside 在 hesperidinase 作用下， 以 水 为溶剂， 反应 72.0h， 以1.4 mg的产率得到5-endo-hydroxy-1,7,7-trimethylbicyclo<2.2.1>heptan-2-one
  参考文献：
  名称：

  Terpene Glycosides and Cytotoxic Constituents from the Seeds ofAmomum xanthioides

  摘要：

  通过柱色谱分离 Amomum xanthioides 种子的 MeOH 提取物，得到了一种新的二萜糖苷 amoxanthoside A (1)，两种新的单萜糖苷 (1S,4S,5S)-5-exo-hydroxycamphor 5-O-β-D-glucopyranoside (2) 和 (1R,4R,5S)-5-endo-hydroxycamphor 5-O-β-D-glucopyranoside (3)、4R,5S)-5-endo-hydroxycamphor 5-O-β-D-glucopyranoside (3)，以及四种已知化合物：hedychiol A (4)、pygmol (5)、(1S,4R,6R)-(+)-6-endo-hydroxycamphor (6) 和 dihydroyashabushiketol (7)。新化合物的结构是通过光谱分析（包括大量二维核磁共振数据）确定的。利用磺胺 B 生物测定法测试了分离出的化合物对四种人类癌细胞系的体外细胞毒性。

  DOI：

  10.1055/s-0029-1186194

文献信息

• Exploring the substrate specificity of Cytochrome P450cin
  作者：Jeanette E. Stok、Peter D. Giang、Siew Hoon Wong、James J. De Voss

  DOI：10.1016/j.abb.2019.07.025

  日期：2019.9

  Initial screening indicated that P450cin could catalyse the oxidation of most of the monoterpenes tested; however, sesquiterpenes were not substrates for this enzyme or the N242A mutant. Additionally, both P450cin mutants were found to be able to oxidise other bicyclic monoterpenes. For example, the oxidation of (R)- and (S)-camphor by N242T favoured the production of 5-endo-hydroxycamphor (65-77% of the

  细胞色素P450是催化多种化合物氧化的酶，这些化合物从较小的挥发性化合物（如单萜）到较大的化合物（如类固醇）不等。可以对这些酶进行修饰，以选择性地氧化感兴趣的底物，从而使其在生物技术工业中的应用具有吸引力。在这项研究中，我们筛选了一个针对P450cin和两个P450cin突变体N242A和N242T的萜烯和类萜化合物的小文库，先前已证明它们会影响选择性。初步筛选表明，P450cin可以催化大多数测试的单萜的氧化。然而，倍半萜烯不是该酶或N242A突变体的底物。另外，发现两个P450cin突变体都能够氧化其他双环单萜。例如，N242T对（R）和（S）樟脑的氧化作用有利于生成5-内羟基樟脑（总产物的65-77％，取决于对映异构体），这与以前对（R ）-用N242A（73％）制成的樟脑。还观察到（R）-和（S）-柠檬烯的选择性，其中N242A主要产生顺式-柠檬烯1,2-环氧化物（（R）-柠檬烯氧
• In vivo and in vitro hydroxylation of cineole and camphor by cytochromes P450CYP101A1, CYP101B1 and N242A CYP176A1
  作者：Jeanette E. Stok、Emma A. Hall、Isobella S.J. Stone、Margaret C. Noble、Siew Hoon Wong、Stephen G. Bell、James J. De Voss

  DOI：10.1016/j.molcatb.2016.03.004

  日期：2016.6

  Cytochromes P450 (P450s) are valuable enzymes that can generate a range of useful compounds via biocatalytic oxidations that complement traditional synthetic chemistry. In this study three bacterial P450s, qP450(cam) (CYP101A1), CYP101B1 and the mutant N242A-P450(cin) (N242A-CYP176A1), were used to produce a range of products from the oxidation of the monoterpenes (1R)- and (1S) -camphor and 1,8-cineole. We demonstrate that both in vitro and in vivo catalytic turnover with these P450s can produce a complement of up to seven hydroxycamphors and seven hydroxycineoles, in addition to compounds produced from further oxidation. The CYP101B1 whole cell catalytic system was found to produce 300-600 mg/L of culture of oxidation products that could be easily separated chromatographically. The CYP101B1 in vitro oxidation of 1,8-cineole primarily produced (1S)-5 alpha-hydroxycineole, which was 78% of the total product formed. However, the amount of (1S)-5a-hydroxycineole was reduced to 42% of the total products when isolated from the CYP101B1 whole cell system. (1S)-6 alpha-Hydroxycineole (96% ee) could be isolated from a whole cell catalytic turnover of 1,8-cineole by N242A-P450c,n in a yield of 46 mg/L (98% of the total product). However, the amount of product isolated ((1R)-5-endo-hydroxycamphor, 75% of the total products) from the whole cell catalytic oxidation of (1R) -camphor with N242A-P450c,n was much lower (6 mg/L) due to the inefficient use of reducing equivalents (3.5 + 0.5%) for substrate oxidation. These compounds will assist in the identification of specific structures in mechanistic investigations and structure elucidation, but further optimisation is required to generate larger quantities for synthetic applications. (C) 2016 Elsevier B.V. All rights reserved.
• MICROBIOLOGICAL DEGRADATION OF (+)-CAMPHOR
  作者：W. H. Bradshaw、H. E. Conrad、E. J. Corey、I. C. Gunsalus、D. Lednicer

  DOI：10.1021/ja01529a060

  日期：1959.10