(1S,2S,4aR,6R,7S,8S,8aR)-7-[tert-butyl(dimethyl)silyl]oxy-2,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbaldehyde | 1417090-97-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (1S,2S,4aR,6R,7S,8S,8aR)-7-[tert-butyl(dimethyl)silyl]oxy-2,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbaldehyde
• CAS: 1417090-97-1
• 化学式: C₂₀H₃₆O₂Si
• 分子量: 336.59
• InChiKey: GTJDMWYXWIJGSP-PHFHYRSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2S,4aR,6R,7S,8S,8aR)-7-[tert-butyl(dimethyl)silyl]oxy-2,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbaldehyde 在 二异丁基氢化铝 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 14.42h， 生成 2E-3-((3S,4S,4aS,5S,6S,7R,8aR)-3,4,4a,5,6,7,8,8a-octahydro-6-(tertbutyldimethylsiloxy)-3,5,7-trimethylnaphthalen-4-yl)prop-2-en-1-ol
  参考文献：
  名称：

  Total Synthesis of AMF-26, an Antitumor Agent for Inhibition of the Golgi System, Targeting ADP-Ribosylation Factor 1

  摘要：

  An effective method for the total synthesis of 1 (AMF-26), a potentially promising new anticancer drug that disrupts the Golgi system by inhibiting the ADP-ribosylation factor 1 (Arf1) activation, has been developed for the first time. The construction of the chiral linear precursor (a key to the synthesis) was achieved by the asymmetric aldol reaction followed by the computer-assisted predictive stereoselective intramolecular Diels-Alder reaction. The global antitumor activity of the totally synthetic 1 against a variety of human cancer cells was assessed using a panel of 39 human cancer cell lines (JFCR39), and it was shown that the synthetic 1 strongly inhibited the growth of several cancer cell lines at concentrations of less than 0.04 mu M. Biological assays of novel derivatives, 26 and 31, which have different side-chains at the C-4 positions in the Delta(1,2)-octalin backbone, disclosed the importance of the suitable structure of the side-chain containing conjugated multidouble bonds.

  DOI：

  10.1021/jm301695c
• 作为产物：
  描述：

  sorbyl bromide 在 2,6-二甲基吡啶 、 lithium aluminium tetrahydride 、 tin(II) trifluoromethanesulfonate 、 四丙基高钌酸铵 、 (R)-1-methyl-2-(1-naphthylaminomethyl)pyrrolidine 、 sodium hexamethyldisilazane 、 四丁基碘化铵 、 二异丁基氢化铝 、 二乙酸二丁基锡 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 93.83h， 生成 (1S,2S,4aR,6R,7S,8S,8aR)-7-[tert-butyl(dimethyl)silyl]oxy-2,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbaldehyde
  参考文献：
  名称：

  JP6143266

  摘要：

  公开号：

文献信息

• Asymmetric Total Synthesis of (+)-Coprophilin
  作者：Isamu Shiina、Yuma Umezaki、Takatsugu Murata、Kyohei Suzuki、Takayuki Tonoi

  DOI：10.1055/s-0036-1591866

  日期：2018.3

  first total synthesis of (+)-coprophilin, an anticoccidial agent, by constructing the chiral linear precursor via a Mukaiyama–Evans aldol reaction and a stereoselective intramolecular Diels–Alder reaction. The proposed method can be used to provide large amounts of (+)-coprophilin, which exhibits a 3,4,5,6,7-pentasubstituted Δ1,2-octalin core structure. In this paper, we report the first total synthesis

  摘要 在本文中，我们通过Mukaiyama–Evans aldol反应和立体选择性分子内Diels–Alder反应构建手性线性前体，从而报告了抗球虫剂（+）-coprophilin的第一个全合成。所提出的方法可以用于提供大量的（+） -对coprophilin，它显示出3,4,5,6,7-五取代Δ 1,2 -octalin芯结构。 在本文中，我们通过Mukaiyama–Evans aldol反应和立体选择性分子内Diels–Alder反应构建手性线性前体，从而报告了抗球虫剂（+）-coprophilin的第一个全合成。所提出的方法可以用于提供大量的（+） -对coprophilin，它显示出3,4,5,6,7-五取代Δ 1,2 -octalin芯结构。
• JP6143266
  申请人：——

  公开号：——

  公开（公告）日：——
• Total Synthesis of AMF-26, an Antitumor Agent for Inhibition of the Golgi System, Targeting ADP-Ribosylation Factor 1
  作者：Isamu Shiina、Yuma Umezaki、Yoshimi Ohashi、Yuta Yamazaki、Shingo Dan、Takao Yamori

  DOI：10.1021/jm301695c

  日期：2013.1.10

  An effective method for the total synthesis of 1 (AMF-26), a potentially promising new anticancer drug that disrupts the Golgi system by inhibiting the ADP-ribosylation factor 1 (Arf1) activation, has been developed for the first time. The construction of the chiral linear precursor (a key to the synthesis) was achieved by the asymmetric aldol reaction followed by the computer-assisted predictive stereoselective intramolecular Diels-Alder reaction. The global antitumor activity of the totally synthetic 1 against a variety of human cancer cells was assessed using a panel of 39 human cancer cell lines (JFCR39), and it was shown that the synthetic 1 strongly inhibited the growth of several cancer cell lines at concentrations of less than 0.04 mu M. Biological assays of novel derivatives, 26 and 31, which have different side-chains at the C-4 positions in the Delta(1,2)-octalin backbone, disclosed the importance of the suitable structure of the side-chain containing conjugated multidouble bonds.