methyl ent-17-hydroxy-16βH-kauran-19-oate | 52020-25-4

• 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: methyl ent-17-hydroxy-16βH-kauran-19-oate
• 英文别名: Methyl-17-hydroxy-16β-ent-kauren-19-oat；methyl (1S,4S,5R,9S,10R,13R,14S)-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
• CAS: 52020-25-4
• 化学式: C₂₁H₃₄O₃
• 分子量: 334.499
• InChiKey: HCXQUFPQHLFUCK-VVIZTZINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl ent-17-hydroxy-16βH-kauran-19-oate 在 萘 、 sodium 作用下， 以 四氢呋喃 为溶剂， 生成 ent-16βH,17-hydroxy-kauran-19-oic acid
  参考文献：
  名称：

  使用酮酸酯类的酰化环合成13-羟基化的ent -kaur-16-ene衍生物

  摘要：

  描述了甜菊醇（27）和两个A环修饰的类似物（9和15）的合成。该合成序列涉及适当地制备构成17去甲13,16-seco- ENT -kauranoid酮酯（22，7和13），其然后环化成13,16-dooxygenated -17-去甲ENT -kauranes（23、8和14）。

  DOI：

  10.1016/0040-4020(76)80050-6
• 作为产物：
  描述：

  kaurenoic acid methyl ester 生成 methyl ent-17-hydroxy-16βH-kauran-19-oate
  参考文献：
  名称：

  Ring C Functionalized Diterpenoids. Part I. The Hypoiodite Reaction as a Route to Ring C Functionalized Kauranes and Phyllocladanes

  摘要：

  在回流环己烷中，16β-ent-17-Kauranol(1a)、相应的C-19酯(1b)和16β,17-Phyllocladanol(2)与四乙酸铅-碘反应，主要发生在C-11的分子内攻击。因此，1a主要产生11-烯-17-醇(3a)和11β-碘-12β,17-醚(4a)，以及少量的9,11-烯-12β,17-醚(5)、11β,17-醚(6a)和由于在C-12处发生攻击而产生的12β,17-醚(7)。Phyllocladanol 2生成了11β,17-醚(8)和9,11-烯-12β,17-醚(9)。将结构6a、7和8归因于它们与四氧化二铑的转化为相应的内酯，即10、11和12。

  DOI：

  10.1139/v73-614

文献信息

• Ring C Functionalized Diterpenoids. Part I. The Hypoiodite Reaction as a Route to Ring C Functionalized Kauranes and Phyllocladanes
  作者：Alan James McAlees、Robert McCrindle

  DOI：10.1139/v73-614

  日期：1973.12.15

  16β-ent-17-Kauranol (1a), the corresponding C-19 ester (1b), and 16β,17-phyllocladanol (2), on reaction with lead tetraacetate – iodine in refluxing cyclohexane, suffered intramolecular attack mainly at C-11. Thus1a gave as major products the 11-en-17-ol (3a) and the 11β-iodo-12β,17-ether (4a), along with minor amounts of the 9,11-en-12β,17-ether (5), the 11β,17-ether (6a), and, resulting from attack at C-12, the 12β,17-ether (7). The phyllocladanol 2 gave the 11β,17-ether (8) and the 9,11-en-12β,17-ether (9). The assignment of structures 6a, 7, and 8 to the ethers rests on their conversion with ruthenium tetroxide into the corresponding lactones, 10, 11, and 12.

  在回流环己烷中，16β-ent-17-Kauranol(1a)、相应的C-19酯(1b)和16β,17-Phyllocladanol(2)与四乙酸铅-碘反应，主要发生在C-11的分子内攻击。因此，1a主要产生11-烯-17-醇(3a)和11β-碘-12β,17-醚(4a)，以及少量的9,11-烯-12β,17-醚(5)、11β,17-醚(6a)和由于在C-12处发生攻击而产生的12β,17-醚(7)。Phyllocladanol 2生成了11β,17-醚(8)和9,11-烯-12β,17-醚(9)。将结构6a、7和8归因于它们与四氧化二铑的转化为相应的内酯，即10、11和12。
• Synthesis, cytotoxicity and antiplasmodial activity of novel ent -kaurane derivatives
  作者：Ronan Batista、Pablo A. García、María Angeles Castro、José M. Miguel del Corral、Nivaldo L. Speziali、Fernando de P. Varotti、Renata C. de Paula、Luis F. García-Fernández、Andrés Francesch、Arturo San Feliciano、Alaíde B. de Oliveira

  DOI：10.1016/j.ejmech.2012.12.010

  日期：2013.4

  This paper reports on the syntheses and spectrometric characterisation of eleven novel ent-kaurane diterpenoids, including a complete set of H-1, C-13 NMR and crystallographic data for two novel ent-kaurane diepoxides. Moreover, the antineoplastic cytotoxicity for kaurenoic acid and the majority of ent-kaurane derivatives were assessed in vitro against a panel of fourteen cancer cell lines, of which allylic alcohols were shown to be the most active compounds. The good in vitro antimalarial activity and the higher selectivity index values observed for some ent-kaurane epoxides against the chloroquine-resistant W2 clone of Plasmodium falciparum indicate that this class of natural products may provide new hits for the development of antimalarial drugs. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Lewis, Norman J.; MacMillan, Jake, Journal of the Chemical Society. Perkin transactions I, 1980, p. 1270 - 1278
  作者：Lewis, Norman J.、MacMillan, Jake

  DOI：——

  日期：——
• The synthesis of 13-hydroxylated ent-kaur-16-ene derivatives using an acyloin-like cyclization of keto esters
  作者：I.F. Cook、J.R. Knox

  DOI：10.1016/0040-4020(76)80050-6

  日期：1976.1

  The synthesis of steviol (27) and two A-ring modified analogues (9 and 15) is described. The synthetic sequences involve the preparation of suitably constituted 17-nor-13,16-seco-ent-kauranoid keto esters (22, 7 and 13) which are then cyclized to 13,16-dooxygenated-17-nor-ent-kauranes (23, 8 and 14).

  描述了甜菊醇（27）和两个A环修饰的类似物（9和15）的合成。该合成序列涉及适当地制备构成17去甲13,16-seco- ENT -kauranoid酮酯（22，7和13），其然后环化成13,16-dooxygenated -17-去甲ENT -kauranes（23、8和14）。
• Bioinspired Synthesis of Platensimycin from Natural <i>ent</i>-Kaurenoic Acids
  作者：Álvaro Pérez、José F. Quílez del Moral、Alberto Galisteo、Juan M. Amaro、Alejandro F. Barrero

  DOI：10.1021/acs.orglett.3c01470

  日期：2023.7.28

  The biomimetic formal synthesis of the antibiotic platensimycin for the treatment of infection by multidrug-resistant bacteria was accomplished starting from either ent-kaurenoic acid or grandiflorenic acid, each of which is a natural compound available in multigram scale from its natural source. Apart from the natural origin of the selected precursors, the keys of the described approach are the long-distance

  用于治疗多重耐药细菌感染的抗生素平板霉素的仿生正式合成是从对映贝壳杉烯酸或大花烯酸开始完成的，这两种酸都是来自其天然来源的多克规模的天然化合物。除了所选前体的天然来源外，所述方法的关键是对映贝壳杉烯酸在 C11处的长距离官能化以及二萜框架 A 环降解的有效方案。