(4aS,6S,8aS)-5,5,8a-trimethyloctahydro-2H-spiro[naphthalene-1,2'-[1,3]dioxolan]-6-ol | 113666-03-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aS,6S,8aS)-5,5,8a-trimethyloctahydro-2H-spiro[naphthalene-1,2'-[1,3]dioxolan]-6-ol
• 英文别名: (2'S,4'aS,8'aS)-1',1',4'a-trimethylspiro[1,3-dioxolane-2,5'-3,4,6,7,8,8a-hexahydro-2H-naphthalene]-2'-ol
• CAS: 113666-03-8
• 化学式: C₁₅H₂₆O₃
• 分子量: 254.37
• InChiKey: OHHWWEHQVYBIRK-OBJOEFQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4aS,6S,8aS)-5,5,8a-trimethyloctahydro-2H-spiro[naphthalene-1,2'-[1,3]dioxolan]-6-ol 在 正丁基锂 、 偶氮二异丁腈 、 三正丁基氢锡 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 、 丙酮 、 xylene 为溶剂， 反应 2.58h， 生成 (+-)-5,5,8a-trimethyl-(4ar,8at)-octahydro-naphthalen-1-one
  参考文献：
  名称：

  Hagiwara, Hisahiro; Nagatomo, Hidenori; Kazayama, Shin-Ichi, Journal of the Chemical Society. Perkin transactions I, 1999, # 4, p. 457 - 459

  摘要：

  DOI：
• 作为产物：
  描述：

  2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione 在 sodium tetrahydroborate 、 氨 、 potassium formate 、 lithium 、 对甲苯磺酸 、 三乙胺 、 L-脯氨酸 作用下， 以 四氢呋喃 、 丙醇 、 乙醇 、 水 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 147.0h， 生成 (4aS,6S,8aS)-5,5,8a-trimethyloctahydro-2H-spiro[naphthalene-1,2'-[1,3]dioxolan]-6-ol
  参考文献：
  名称：

  Synthesis of the ABC skeleton of the aglycon of Echinoside A

  摘要：

  Echinoside A is a triterpene saponin isolated from the sea cucumber Actinopyga echinites (JAEGER), which displays potent antitumor activities in vitro and in vivo. Here, we report the synthesis of the ABC-fused ring skeleton of the aglycon of Echinoside A, with the enantiomerically pure (+)-Wieland-Miescher ketone being used as starting material and a Robinson annulation as the key reaction. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2015.08.010

文献信息

• Pinacol Coupling Strategy for the Construction of the Bicyclo[6.4.1]tridecane Framework of Schiglautone A
  作者：Bettina Werner、Markus Kalesse

  DOI：10.1021/acs.orglett.7b00288

  日期：2017.4.7

  The synthesis of the tricyclic carbon framework of schiglautone A (1) is reported herein. The generation of the bicyclo[6.4.1]tridecane 19 was accomplished via a SmI2-mediated pinacol coupling of dialdehyde 18. The side chain in 18 was introduced using a selective 1,4-addition. A further key step of the synthesis was the homologation of a Wieland–Miescher ketone derivative to establish the 7-membered

  本文报道了紫草酮A（1）的三环碳骨架的合成。双环[6.4.1]十三烷19的生成是通过SmI 2介导的二醛18频哪醇偶联实现的。使用选择性的1，4-加成法引入18中的侧链。合成的另一个关键步骤是Wieland-Miescher酮衍生物的同系物以建立7元环。
• Nature-inspired development of unnatural meroterpenoids as the non-toxic anti-colon cancer agents
  作者：Md Ashraful Haque、Bethsebie L. Sailo、Ganesan Padmavathi、Ajaikumar B. Kunnumakkara、Chandan K. Jana

  DOI：10.1016/j.ejmech.2018.08.088

  日期：2018.12

  effective against the human colon adenocarcinoma cells with IC50 concentrations of 7.5–20 μM. In this series, the carbotetracyclic catechol 4e (IC50 = 7.5 μM) and quinone 12 (IC50 = 8 μM) were found to be the most potent compounds having the IC50 of less than 10 μM with no cytotoxic effect on the normal cells. Downregulation of Cox-2 and survivin and cell cycle arrest eventually leading to apoptosis were

  从Wieland-Miescher酮衍生物开始合成抗癌天然产物dysideanone的结构类似物。已经进行了体外研究以评估这些非天然的类萜对结肠癌的抗癌潜力。与它们的无环甲醇衍生物相比，发现合成的碳四环化合物具有更高的活性。发现非天然碳四环化合物4b-e，4h，4i和12对人结肠腺癌细胞具有高度有效的作用，其IC 50浓度为7.5–20μM。在这个系列中，四环邻苯二酚4e（IC 50  = 7.5μM ）和醌12（IC 50 （= 8μM）是最有效的化合物，IC 50小于10μM，对正常细胞无细胞毒性作用。发现Cox-2和Survivin的下调以及最终导致细胞凋亡的细胞周期停滞是这些非天然类萜的抗癌作用的潜在机制。
• Enantioselective first total syntheses of the antiviral natural products xiamycins D and E
  作者：Dattatraya H. Dethe、Manmohan Shukla

  DOI：10.1039/d1cc04739f

  日期：——

  The enantioselective first total syntheses of marine pentacyclic indolosesquiterpenoids xiamycins D (4) and E (5) have been described for the first time to the best of our knowledge. The synthetic approach was designed to feature functionalization of enantiopure Wieland–Miescher ketone, Michael addition followed by Heck-type annulation/aromatization, regioselective sp3(C–H) activation, benzylic oxidation

  据我们所知，首次描述了海洋五环吲哚倍半萜类物质夏霉素 D ( 4 ) 和 E ( 5 )的对映选择性首次全合成。该合成方法旨在实现对映体纯 Wieland-Miescher 酮的功能化、迈克尔加成，然后是 Heck 型环化/芳构化、区域选择性 sp 3 (C-H) 活化、苄基氧化和非对映选择性还原。
• Enantioselective Synthesis and Complement Inhibitory Assay of A/B-Ring Partial Analogues of Oleanolic Acid
  作者：Haregewein Assefa、Alison Nimrod、Larry Walker、Robert Sindelar

  DOI：10.1016/s0960-894x(01)00210-4

  日期：2001.7

  A series of oleanolic acid A/B-ring partial analogues was synthesized and tested for their complement inhibitory activity as well as cytotoxic properties. All target compounds and one intermediate exhibited moderate complement inhibitory potency. These compounds also showed cytotoxicity on malignant melanoma cell line, SK-MEL. (C) 2001 Elsevier Science Ltd. All rights reserved.
• One-Pot Relay Gold(I) and Brønsted Acid Catalysis: Cyclopenta[<i>b</i>]annulation of Indoles via Hydroamination/Nazarov-Type Cyclization Cascade of Enynols
  作者：Seema Dhiman、S. S. V. Ramasastry

  DOI：10.1021/acs.orglett.5b02632

  日期：2015.10.16

  An expedient relay gold(I) and Bronsted acid catalyzed hydroamination/Nazarov cyclization of 1-(2-aminophenyl)pent-4-en-2-ynols for the synthesis of various polyfunctionalized cyclopenta[b]indoles is described. The synthetic utility of this method has been demonstrated by the synthesis of a few unprecedented pentacyclic indoles and indole steroidal hybrids. Further, the new methodology has been successfully applied to the enantioselective synthesis of core carbon structure of the polyveoline family of natural products.