(1S,2S,4aS,8aS)-2,5,5,8a-tetramethyldecahydronaphthalen-1-carbaldehyde | 199438-55-6

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 英文名称: (1S,2S,4aS,8aS)-2,5,5,8a-tetramethyldecahydronaphthalen-1-carbaldehyde
• 英文别名: (1S,2S,4aS,8aS)-2,5,5,8a-tetramethyl-1,2,3,4,4a,6,7,8-octahydronaphthalene-1-carbaldehyde
• CAS: 199438-55-6
• 化学式: C₁₅H₂₆O
• 分子量: 222.371
• InChiKey: MFPHXBWICWFVFG-PWNZVWSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,2S,4aS,8aS)-2,5,5,8a-tetramethyldecahydronaphthalen-1-carbaldehyde 在 叔丁基锂 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 15.25h， 生成 8S-1,2-di-O-benzyl-3-(9'-drimen-11'-yl)-4-O-methylbenzenetriol
  参考文献：
  名称：

  Synthesis of wiedendiol-A and wiedendiol-B from labdane diterpenes

  摘要：

  Two efficient enantiospecific syntheses of wiedendiol-A (1) from (-)-sclareol (7), via 11-bromo-8-drimene (11) and 8-drimen-11-al (3), are reported. The first enantiospecific synthesis of wiedendiol-B (2), via 8S,9S-driman-11-al (26), by two alternative routes starting from 7 and (+)-cis-abienol (8) is also described. 21 prepared from protocatechualdehyde (17) was used as aromatic synthon for preparing 1 and 2. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00235-x
• 作为产物：
  描述：

  (-)-补身醇 在 platinum(IV) oxide 、 草酰氯 、 氢气 作用下， 以 二氯甲烷 、 二甲基亚砜 、 乙酸乙酯 为溶剂， 反应 1.5h， 生成 (1S,2S,4aS,8aS)-2,5,5,8a-tetramethyldecahydronaphthalen-1-carbaldehyde
  参考文献：
  名称：

  (-)-Siphonodictyal B 和 (+)-8-epi-Siphonodictyal B 与磷脂酰肌醇 3-激酶 α (PI3Kα) 抑制活性的对映选择性全合成

  摘要：

  具有生物学意义的海洋类萜 (–)-siphonodictyal B 和 (+)-8-epi-siphonodictyal B 以 29–40% 的总产率在最长的 11 步线性序列中有效合成. 合成涉及以下关键步骤：（i）高烯丙基萘烷醇的立体发散氢化以安装存在于萘烷片段中的必需的 C8 立体中心；(ii) 将十氢萘片段与芳香部分偶联以组装所需的碳骨架；(iii) 从芳环上的多个O-保护基团上脱保护以完成项目合成。(-)-siphonodictyal B 和 (+)-8-epi-siphonodictyal B 均显示出 PI3Kα 抑制活性，其效力与 liphagal（一种天然存在的 PI3Kα 抑制剂）相当。

  DOI：

  10.1002/ejoc.201600949

文献信息

• Total Synthesis and Structure Revision of (−)-Siphonodictyal B and Its Biomimetic Conversion into (+)-Liphagal
  作者：Adrian W. Markwell-Heys、Kevin K. W. Kuan、Jonathan H. George

  DOI：10.1021/acs.orglett.5b01973

  日期：2015.9.4

  reassigned on the basis of the total synthesis of both possible C-8 epimers. The revised structure of siphonodictyal B was converted into liphagal by acid catalyzed rearrangement of a proposed epoxide intermediate. This biomimetic cascade features a succession of four distinct reactions (epoxidation, o-quinone methide formation, ring expansion, and benzofuran formation) that occur in a one-pot operation

  在两种可能的C-8差向异构体的总合成的基础上，虹吸式乙的结构已被重新分配。通过酸催化重排拟议的环氧中间体，将虹吸管B的结构修改为脂状。这种仿生级联反应的特征是在温和条件下在一锅操作中发生的四个不同的反应（环氧化，邻醌甲基化物形成，环膨胀和苯并呋喃形成）。在这些研究中，我们还分离出了出乎意料的稳定的邻醌甲基化物，该产物支持了我们有关脂类生物合成的机制建议。
• Enantiospecific Synthesis of Wiedendiol-B from (−)-Sclareol and (+)-cis-Abienol
  作者：Alejandro F. Barrero、Enrique J. Alvarez-Manzaneda、Rachid Chahboun

  DOI：10.1016/s0040-4039(97)10119-8

  日期：1997.11

  The first enantiospecific synthesis of the cholesteryl ester transfer protein (CETP) inhibitor wiedendiol-B (1) is described. The drimanic synthon was prepared from (-)-sclareol (4) and (+)-cis-abienol (13) by two alternative routes. The key steps of the reaction sequences are the chemo-and diastereoselective hydrogenation of the C-8-C-9 double bond of enal 6 and the stereoselective cationic hydrogenation of the hydroxyl group of 13, respectively, and the selective reduction of benzyl groups of 15. (C) 1997 Elsevier Science Ltd.
• LIPHAGAL ANALOG AND MULTI-TARGETED KINASE INHIBITOR CONTAINING LIPHAGAL OR ANALOG THEREOF
  申请人：TOHOKU UNIVERSITY

  公开号：US20210198271A1

  公开（公告）日：2021-07-01

  Provided is an inhibitor for at least one kind of kinase selected from the group consisting of CDK7, CDK4, CDK6, PIM2, TSSK3, MST4, NEK6, MAP3K, MST3, DDR1, SPHK1, CaMK1, AurA, BRK, CaMK4, and PIM1, the inhibitor including as an active ingredient a compound represented by the following general formula (1) or a salt thereof: in the general formula (1), R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are as described in Description.
• Synthesis of wiedendiol-A and wiedendiol-B from labdane diterpenes
  作者：Alejandro F. Barrero、Enrique J. Alvarez-Manzaneda、Rachid Chahboun

  DOI：10.1016/s0040-4020(98)00235-x

  日期：1998.5

  Two efficient enantiospecific syntheses of wiedendiol-A (1) from (-)-sclareol (7), via 11-bromo-8-drimene (11) and 8-drimen-11-al (3), are reported. The first enantiospecific synthesis of wiedendiol-B (2), via 8S,9S-driman-11-al (26), by two alternative routes starting from 7 and (+)-cis-abienol (8) is also described. 21 prepared from protocatechualdehyde (17) was used as aromatic synthon for preparing 1 and 2. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• Enantioselective Total Synthesis of (-)-Siphonodictyal B and (+)-8-<i>epi</i>-Siphonodictyal B with Phosphatidylinositol 3-Kinase α (PI3Kα) Inhibitory Activity
  作者：Takuya Kikuchi、Koichi Narita、Ken Saijo、Chikashi Ishioka、Tadashi Katoh

  DOI：10.1002/ejoc.201600949

  日期：2016.12

  carbon skeletons; and (iii) deprotection from multiple O-protective groups on the aromatic ring to complete the project synthesis. Both (–)-siphonodictyal B and (+)-8-epi-siphonodictyal B showed PI3Kα inhibitory activity, with potencies comparable to that of liphagal, a naturally occurring PI3Kα inhibitor. New structure–activity relationships for this class of marine meroterpenoids were also revealed.

  具有生物学意义的海洋类萜 (–)-siphonodictyal B 和 (+)-8-epi-siphonodictyal B 以 29–40% 的总产率在最长的 11 步线性序列中有效合成. 合成涉及以下关键步骤：（i）高烯丙基萘烷醇的立体发散氢化以安装存在于萘烷片段中的必需的 C8 立体中心；(ii) 将十氢萘片段与芳香部分偶联以组装所需的碳骨架；(iii) 从芳环上的多个O-保护基团上脱保护以完成项目合成。(-)-siphonodictyal B 和 (+)-8-epi-siphonodictyal B 均显示出 PI3Kα 抑制活性，其效力与 liphagal（一种天然存在的 PI3Kα 抑制剂）相当。