3-methoxy-5,6,7,8,9,10-hexahydrocycloheptindole | 51208-04-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-methoxy-5,6,7,8,9,10-hexahydrocycloheptindole
• 英文别名: 5-Methoxy-2,3-pentamethylen-indol；2-Methoxy-5,6,7,8,9,10-hexahydrocyclohepta[b]indole
• CAS: 51208-04-9
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: IZMJPFWHTLKGEL-UHFFFAOYSA-N

物化性质

• 熔点：
  122-124 °C
• 沸点：
  378.4±37.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-methoxy-5,6,7,8,9,10-hexahydrocycloheptindole 在 三氯化铝 、 苄硫醇 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 1,2,3,4-tetrahydro-6-hydroxy-9-methylcarbazole
  参考文献：
  名称：

  Novel Indole-2-carboxamide and Cycloalkeno[1,2-b]indole Derivatives. Structure−Activity Relationships for High Inhibition of Human LDL Peroxidation

  摘要：

  Series of indole-2-carboxamide and cycloalkeno[1,2-b]indole derivatives were synthesized and evaluated in order to determine the necessary structural requirements for a high inhibition of human LDL copper-induced peroxidation. Various modulations were systematically performed on the indole and cycloalkeno[1,2-b]indole nuclei as well as on the carboxamide moiety. The best compounds (3c, 3e, 7c, 7f, 7h, 7g, and 7o) are between 5 and 30 times more active than probucol itself. Two of these compounds (3c and 70) were selected for complementary in vitro and in vivo investigations, which have shown additional properties of interest for the treatment and the prevention of atherosclerosis injuries. Compound 3e was found to have some antiinflammatory properties while compound 70 was proved to protect endothelial cells from the direct cytotoxicity of oxidized LDL with some additional calcium channel blocking properties.

  DOI：

  10.1021/jm960542k
• 作为产物：
  描述：

  3-氯-4-甲氧基苯胺 在 sodium amide 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 40.0h， 生成 3-methoxy-5,6,7,8,9,10-hexahydrocycloheptindole
  参考文献：
  名称：

  Aggregative activation and heterocyclic chemistry I complex bases promoted arynic cyclisation of imines or enaminoketones; regiochemical synthesis of indoles

  摘要：

  The complex base NaNH2-t-BuONa allowed expeditious syntheses of indoles by arynic cyclisation of imines or enaminoketones prepared from halogeno anilines and carbonyl derivatives. Unstable imines may be used without purification, complex bases being unsensitive to impurities. It is showed that this kind of reaction may be applied to mixture of substrates suitably halogenated on the benzene ring. Formation of three components aggregates is proposed to explain a number of observations.

  DOI：

  10.1016/s0040-4020(01)89304-2

文献信息

• Auto-tandem PET and EnT photocatalysis by crude chlorophyll under visible light towards the oxidative functionalization of indoles
  作者：Saira Banu、Shubham Choudhari、Girija Patel、Prem P. Yadav

  DOI：10.1039/d1gc00138h

  日期：——

  Chlorophyll is the most abundant photocatalytic pigment that enables plants to absorb solar energy and convert it to energy storage molecules. Herein, we report a tandem photocatalytic approach utilizing the natural pigment chlorophyll in crude form to achieve photoinduced electron transfer (PET) and energy transfer (EnT) towards the oxidative functionalization of indoles. Redox potentials, ESR, fluorescence

  叶绿素是最丰富的光催化颜料，使植物能够吸收太阳能并将其转化为能量存储分子。在本文中，我们报告了一种串联光催化方法，该方法利用天然形式的天然色素叶绿素实现了对吲哚的氧化功能化的光致电子转移（PET）和能量转移（EnT）。氧化还原电势，ESR，荧光猝灭和紫外线实验已经证明了叶绿素的双重催化活性。该研究的重点是叶绿素的自动串联光催化作用，以分子氧作为氧化剂，水作为反应介质，并利用光谱可见区的光化学能，使吲哚绿色氧化。
• A Variation of the Fischer Indolization Involving Condensation of Quinone Monoketals and Aliphatic Hydrazines
  作者：Jinzhu Zhang、Zhiwei Yin、Patrick Leonard、Jing Wu、Kate Sioson、Che Liu、Robert Lapo、Shengping Zheng

  DOI：10.1002/anie.201207533

  日期：2013.2.4

  new twist: A one‐pot nitrous acid free, diazonium‐free, and transition‐metal‐free variation of the Fischer indole synthesis has been developed. Condensation of quinone monoketals and aliphatic hydrazine hydrochlorides afforded indoles via intermediate alkylaryldiazenes. This method will complement the classical Fischer indole synthesis by providing indoles in two steps from widely available phenols

  一个新的转折：已开发出Fischer吲哚合成的一锅无亚硝酸，无重氮和无过渡金属的变体。醌单缩酮和脂族肼盐酸盐的缩合通过中间体烷基芳基二氮烯得​​到吲哚。该方法将在温和的条件下从两步制得的苯酚中分两步提供吲哚，从而补充了经典的Fischer吲哚合成方法。
• Visible‐Light Cascade Photooxygenation of Tetrahydrocarbazoles and Cyclohepta[ <i>b</i> ]indoles: Access to <i>C</i> , <i>N</i> ‐Diacyliminium Ions
  作者：Mario Frahm、Thorsten Drathen、Lisa Marie Gronbach、Alice Voss、Felix Lorenz、Jonas Bresien、Alexander Villinger、Frank Hoffmann、Malte Brasholz

  DOI：10.1002/anie.202007549

  日期：2020.7.20

  Tetrahydrocarbazoles and perhydrocyclohepta[b]indoles undergo a catalytic cascade singlet oxygenation in alkaline medium, which leads to chiral tricyclic perhydropyrido‐ and perhydroazepino[1,2‐a]indoles in a single operation. These photooxygenation products are new synthetic equivalents of uncommon C,N‐diacyliminium ions and can be functionalized with the aid of phosphoric acid organocatalysis.

  四氢咔唑和全氢环庚[b]吲哚在碱性介质中经历催化级联单线态氧合反应，这会在一次操作中导致手性三环全氢吡啶并全氢哌啶[1,2-a]吲哚。这些光氧化产物是不常见的C，N-二酰基亚胺离子的新合成等价物，可以借助磷酸有机催化进行功能化。
• Rhodium-Catalyzed Synthesis of 2,3-Disubstituted Indoles from β,β-Disubstituted Stryryl Azides
  作者：Ke Sun、Sheng Liu、Patryk M. Bec、Tom G. Driver

  DOI：10.1002/anie.201006917

  日期：2011.2.11

  Rings à la carte: Rhodium carboxylate complexes catalyze selective cascade reactions to produce a range 2,3‐disubstituted indoles from β,β‐disubstituted stryryl azides. The selective migration of aryl groups appears to originate from a putative phenonium ion reactive intermediate (see scheme).

  点菜环：羧酸铑配合物催化选择性级联反应，从 β,β-二取代苯乙烯基叠氮化物产生一系列 2,3-二取代吲哚。芳基的选择性迁移似乎源自假定的苯鎓离子反应中间体（参见方案）。
• Enantioselective gold catalyzed dearomative [2+2]-cycloaddition between indoles and allenamides
  作者：Minqiang Jia、Magda Monari、Qing-Qing Yang、Marco Bandini

  DOI：10.1039/c4cc08736d

  日期：——

  The missing l(r)ink(g): a series of densely substituted 2,3-cyclobutane-fused indolines is obtained in a highly stereocontrolled manner via enantioselective [Au(i)]-catalyzed formal [2+2]-cycloaddition reactions between indoles and allenamides.

  缺失的「l」（r）「ink」（g）：一系列密度取代的2,3-环丁烷-融合吲哚烷以高度立体控制的方式通过对吲哚和异戊二烯酰胺进行手性选择性[Au(i)]催化的正式[2+2]-环加成反应获得。