(E)-1-(4,8-dimethylnona-3,7-dien-1-yl)naphthalene | 1388152-53-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-1-(4,8-dimethylnona-3,7-dien-1-yl)naphthalene
• 英文别名: 1-[(3E)-4,8-dimethylnona-3,7-dienyl]naphthalene
• CAS: 1388152-53-1
• 化学式: C₂₁H₂₆
• 分子量: 278.437
• InChiKey: HCVSAUNPBWXFTR-WOJGMQOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (E)-1-(4,8-dimethylnona-3,7-dien-1-yl)naphthalene 在 (R)-3,3'-dichloro-1,1'-binaphthalene-2,2'-diol 、 氯化锑(V) 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到(4aS,10aS)-1,1,4a-trimethyl-1,2,3,4,4a,11,12,12a-octahydrochrysene
  参考文献：
  名称：

  Highly Enantioselective Proton-Initiated Polycyclization of Polyenes

  摘要：

  This report describes the synthesis of a range of chiral polycyclic molecules (tricyclic to pentacyclic) from achiral polyene precursors by enantio-selective proton-initiated polycyclization promoted by the 11 complex of o,o'-dichloro-BINOL and SbCl5. Excellent yields (ca. 90% per ring formed) and enantioselectivety (20:1 to 50:1) were obtained. The process is practical as well as efficient, because the chiral ligand is both readily prepared from R,R- or S,S-BINOL and easily recovered from the reaction mixture by extraction.

  DOI：

  10.1021/ja305851h
• 作为产物：
  描述：

  1-萘甲醇 在 吡啶 、 氯化亚砜 、 sodium dihydrogenphosphate dihydrate 、 sodium amalgam 、 四丁基溴化铵 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 、 丙酮 、 苯 为溶剂， 反应 18.33h， 生成 (E)-1-(4,8-dimethylnona-3,7-dien-1-yl)naphthalene
  参考文献：
  名称：

  对映选择性、路易斯碱催化的多烯硫环化

  摘要：

  描述了硫鎓离子引发的催化对映选择性多烯环化。同香叶基芳烃和邻香叶基酚以良好的收率、非对映选择性和对映选择性进行多环化。立体决定步骤是在手性路易斯碱性催化剂存在下，由末端烯烃和磺化剂生成对映体富集的噻喃离子。使用六氟异丙醇作为溶剂对于获得良好的产率至关重要。反应产生的硫醚部分随后可以在环化后转化为不同的氧和碳官能团。 (+)-ferruginol 和 (+)-hinokiol 的对映选择性合成证明了该方法的实用性。

  DOI：

  10.1021/jacs.8b01660

文献信息

• A two-step mimic for direct, asymmetric bromonium- and chloronium-induced polyene cyclizations
  作者：Scott A. Snyder、Daniel S. Treitler、Andreas Schall

  DOI：10.1016/j.tet.2010.03.037

  日期：2010.6

  Although direct, asymmetric, halonium-induced cyclizations have proven difficult to achieve in the absence of enzymes, this report provides a two-step alternative based on reacting polyenes with chiral mercury(II) complexes to afford a number of polycyclic organomercurials that can be subsequently converted, with retention, into their corresponding chlorine, bromine, and iodine derivatives in good

  尽管事实证明，在不存在酶的情况下，直接，不对称，ha诱导的环化很难实现，但本报告提供了一种基于多烯与手性汞（II）配合物反应的两步替代方法，从而提供了许多可随后被应用的多环有机汞。以高收率和对映选择性将其保留后转化为其相应的氯，溴和碘衍生物。还描述了天然产物4-异环巴巴多醇的五步不对称全合成。
• “Phosphite–urea” cooperative high-turnover catalysts for the highly selective bromocyclization of homogeranylarenes
  作者：Yasuhiro Sawamura、Hidefumi Nakatsuji、Akira Sakakura、Kazuaki Ishihara

  DOI：10.1039/c3sc51432c

  日期：——

  Nucleophilic phosphite–urea cooperative high-turnover catalysts have been designed for the highly selective bromocyclization of homogeranylarenes. The introduction of a urea moiety and bulky aryl groups in the catalyst inhibits decomposition of the catalyst and the generation of byproducts. Only 0.5 mol% of the catalyst successfully promotes the bromocyclization of 4-homogeranyltoluene to give the

  亲核亚磷酸酯–尿素已经设计了合作的高周转催化剂，用于高geranyanylarenes的高选择性溴环化。在催化剂中引入脲部分和庞大的芳基会抑制催化剂的分解和副产物的产生。仅0.5mol％的催化剂成功地促进了4-高茂基甲苯的溴环化，以96％的收率得到了所需的产物。
• Two Unprecedented Reactions of Nitrosyl Triflate: NO⁺-Induced Cationic Cascade Cyclization and C═C Oxidative Cleavage
  作者：G. Sudhakar Reddy、E. J. Corey

  DOI：10.1021/acs.orglett.3c00353

  日期：2023.3.24

  Nitrosyl triflate is shown to react with olefins in a CH2Cl2 solution by three different pathways depending on structure and reaction conditions: (1) cationic cyclization, (2) C═C cleavage, and (3) allylic nitrosation. Possible reaction pathways are described.

  根据结构和反应条件，亚硝酰三氟甲磺酸酯在 CH 2 Cl 2溶液中通过三种不同途径与烯烃反应：(1) 阳离子环化，(2) C=C 裂解，和 (3) 烯丙基亚硝化。描述了可能的反应途径。
• Enantioselective, Lewis Base-Catalyzed Sulfenocyclization of Polyenes
  作者：Zhonglin Tao、Kevin A. Robb、Kuo Zhao、Scott E. Denmark

  DOI：10.1021/jacs.8b01660

  日期：2018.3.14

  Homogeranylarenes and ortho-geranylphenols undergo polycyclization in good yield, diastereoselectivity, and enantioselectivity. The stereodetermining step is the generation of an enantiomerically enriched thiiranium ion from a terminal alkene and a sulfenylating agent in the presence of a chiral Lewis basic catalyst. The use of hexafluoroisopropyl alcohol as the solvent is crucial to obtain good yields

  描述了硫鎓离子引发的催化对映选择性多烯环化。同香叶基芳烃和邻香叶基酚以良好的收率、非对映选择性和对映选择性进行多环化。立体决定步骤是在手性路易斯碱性催化剂存在下，由末端烯烃和磺化剂生成对映体富集的噻喃离子。使用六氟异丙醇作为溶剂对于获得良好的产率至关重要。反应产生的硫醚部分随后可以在环化后转化为不同的氧和碳官能团。 (+)-ferruginol 和 (+)-hinokiol 的对映选择性合成证明了该方法的实用性。
• Highly Enantioselective Proton-Initiated Polycyclization of Polyenes
  作者：Karavadhi Surendra、E. J. Corey

  DOI：10.1021/ja305851h

  日期：2012.7.25

  This report describes the synthesis of a range of chiral polycyclic molecules (tricyclic to pentacyclic) from achiral polyene precursors by enantio-selective proton-initiated polycyclization promoted by the 11 complex of o,o'-dichloro-BINOL and SbCl5. Excellent yields (ca. 90% per ring formed) and enantioselectivety (20:1 to 50:1) were obtained. The process is practical as well as efficient, because the chiral ligand is both readily prepared from R,R- or S,S-BINOL and easily recovered from the reaction mixture by extraction.