(S)-8a'-methyl-5'-(phenylthiomethyl)-3',4',8',8a'-tetrahydro-2'H-spiro[[1,3]dioxolane-2,1'-naphthalen]-6'(7'H)-one | 91444-85-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (S)-8a'-methyl-5'-(phenylthiomethyl)-3',4',8',8a'-tetrahydro-2'H-spiro[[1,3]dioxolane-2,1'-naphthalen]-6'(7'H)-one
• 英文别名: (4'aS)-4'a-methyl-1'-(phenylsulfanylmethyl)spiro[1,3-dioxolane-2,5'-4,6,7,8-tetrahydro-3H-naphthalene]-2'-one
• CAS: 91444-85-8
• 化学式: C₂₀H₂₄O₃S
• 分子量: 344.475
• InChiKey: BHHPUUOZNJGFIU-IBGZPJMESA-N

物化性质

• 沸点：
  494.3±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-8a'-methyl-5'-(phenylthiomethyl)-3',4',8',8a'-tetrahydro-2'H-spiro[[1,3]dioxolane-2,1'-naphthalen]-6'(7'H)-one 在 盐酸 、 氢氧化钾 、 氨 、 lithium 、 肼 作用下， 以 四氢呋喃 为溶剂， 反应 15.25h， 生成 (+-)-5,5,8a-trimethyl-(4ar,8at)-octahydro-naphthalen-1-one
  参考文献：
  名称：

  An efficient approach to chiral, nonracemic trans-decahydro-5,8a-dimethyl-1,6-naphthalenedione derivatives. Total synthesis of (+)-pallescensin A

  摘要：

  DOI：

  10.1021/jo00194a003
• 作为产物：
  描述：

  (R)-(-)-8a-甲基-3,4,8,8a-四氢-1,6(2H,7H)-萘二酮 在 对甲苯磺酸 、 三乙胺 作用下， 生成 (S)-8a'-methyl-5'-(phenylthiomethyl)-3',4',8',8a'-tetrahydro-2'H-spiro[[1,3]dioxolane-2,1'-naphthalen]-6'(7'H)-one
  参考文献：
  名称：

  合成与芒果有关的拉丹烷二萜烯作为血小板聚集抑制剂。

  摘要：

  从Wieland-Miescher酮的R-（-）-对映异构体开始，实现了拉丹烷二萜（-）-1的对映选择性全合成。对映异构体（+）-1是通过香紫苏醇的微生物转化通过部分合成获得的。这些结果证实了天然化合物（+）-1，一种血小板凝集抑制剂，具有正常的绝对立体化学，如甘露醇。还使用新型的环收缩反应合成了B-去甲丹烷相关的化合物44。

  DOI：

  10.1248/cpb.41.1698

文献信息

• Nodulisporic Acid A Synthetic Studies. 2. Construction of an Eastern Hemisphere Subtarget
  作者：Amos B. Smith、Young Shin Cho、Haruaki Ishiyama

  DOI：10.1021/ol016888t

  日期：2001.11.1

  In this, the second of two Letters, we describe an effective assembly of (+)-4, an eastern hemisphere subtarget comprising the FGH rings of (+)-nodulisporic acid A (1) (17 steps, 9% overall yield). Central to the synthesis is a Koga three-component conjugate addition-alkylation sequence which secures the trans orientation of the vicinal quaternary methyl groups. [reaction: see text]

  在本文中，这是两个字母的第二个字母，我们描述了（+）-4的有效组装，这是一个包含（+）-去甲孢子酸A（1）的FGH环的东半球子目标（17个步骤，总产率为9％）。合成的中心是Koga三组分共轭加成烷基化序列，可确保邻位季甲基的反式定位。[反应：看文字]
• Development of a Scalable Synthesis of a Common Eastern Tricyclic Lactone for Construction of the Nodulisporic Acids
  作者：Amos B. Smith、László Kürti、Akin H. Davulcu、Young Shin Cho

  DOI：10.1021/op060204l

  日期：2007.1.1

  A scalable, second-generation synthesis of the densely functionalized eastern tricyclic lactone (+)-6, a common intermediate, for construction of the nodulisporic acids has been achieved. Modifications to the first-generation route now permit access to (+)-6 in 17 steps with an overall 16.5% yield. Key carbon-carbon bond constructions include a Kirk-Petrow (phenylthio)methylation, a Sc(OTf)(3)-catalyzed hydroxymethylation, a Stille carbonylation, and a Koga three-component, conjugate addition-alkylation sequence.
• Synthesis of the ABC skeleton of the aglycon of Echinoside A
  作者：Jun Yu、Biao Yu

  DOI：10.1016/j.cclet.2015.08.010

  日期：2015.11

  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.
• Indole diterpene synthetic studies. 2. First-generation total synthesis of (-)-paspaline
  作者：Richard E. Mewshaw、Michael D. Taylor、Amos B. Smith

  DOI：10.1021/jo00275a035

  日期：1989.7
• Shimizu, Takeshi; Hiranuma, Sayoko; Yoshioka, Hirosuke, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 7, p. 1963 - 1965
  作者：Shimizu, Takeshi、Hiranuma, Sayoko、Yoshioka, Hirosuke

  DOI：——

  日期：——