N-[2-(2-iodo-4,5-dimethoxyphenyl)ethyl]carbamic acid ethyl ester | 343780-59-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[2-(2-iodo-4,5-dimethoxyphenyl)ethyl]carbamic acid ethyl ester
• 英文别名: ethyl 2-iodo-4,5-dimethoxyphenethylcarbamate；N-carbethoxy-o-iodohomoveratrylamine；ethyl N-[2-(2-iodo-4,5-dimethoxyphenyl)ethyl]carbamate
• CAS: 343780-59-6
• 化学式: C₁₃H₁₈INO₄
• 分子量: 379.195
• InChiKey: VTMJGJJTJXHJGZ-UHFFFAOYSA-N

物化性质

• 熔点：
  76-78 °C(Solv: methanol (67-56-1))
• 沸点：
  457.9±45.0 °C(Predicted)
• 密度：
  1.492±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[2-(2-iodo-4,5-dimethoxyphenyl)ethyl]carbamic acid ethyl ester 在 palladium diacetate sodium hydride 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 27.0h， 生成 N-(2-{2-[2-(3-isopropoxy-4-methoxyphenyl)vinyl]-4,5-dimethoxyphenyl}ethyl)-N-methylcarbamic acid ethyl ester
  参考文献：
  名称：

  First total syntheses of the 1,2,3,4-tetrahydronaphtho[2,1-f]isoquinolines annoretine and litebamine

  摘要：

  We describe here the first total synthesis of the two natural 1,2,3,4-tetrahydronaphtho[2,1-f]isoquinolines, annoretine and litebamine, from [2-(2-styrylphenyl)ethyl]methylcarbamic acid ethyl esters. The key steps were the Bischler-Napieralski cyclization to form the isoquinoline unit and photocyclization of the resulting 2-methyl-5-styryl-3,4-dihydro-2H-isoquinolin-1-ones to 2-methyl-3,4-dihydro-2H-naphtho[2,1-f]isoquinolin-1-ones. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)01135-9
• 作为产物：
  描述：

  ethyl (3,4-dimethoxyphenethyl)carbamate 在 Barluenga reagent 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以99%的产率得到N-[2-(2-iodo-4,5-dimethoxyphenyl)ethyl]carbamic acid ethyl ester
  参考文献：
  名称：

  First total syntheses of the 1,2,3,4-tetrahydronaphtho[2,1-f]isoquinolines annoretine and litebamine

  摘要：

  We describe here the first total synthesis of the two natural 1,2,3,4-tetrahydronaphtho[2,1-f]isoquinolines, annoretine and litebamine, from [2-(2-styrylphenyl)ethyl]methylcarbamic acid ethyl esters. The key steps were the Bischler-Napieralski cyclization to form the isoquinoline unit and photocyclization of the resulting 2-methyl-5-styryl-3,4-dihydro-2H-isoquinolin-1-ones to 2-methyl-3,4-dihydro-2H-naphtho[2,1-f]isoquinolin-1-ones. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)01135-9

文献信息

• First total synthesis of the 1,2,3,4-tetrahydronaphtho[2,1- f ]isoquinoline annoretine
  作者：M.Carme Pampı́n、Juan C Estévez、Luis Castedo、Ramón J Estévez

  DOI：10.1016/s0040-4039(01)00168-x

  日期：2001.3

  Here we describe the first total synthesis of the 1,2,3,4-tetrahydronaphtho[2,1-f]isoquinoline (6) annoretine from N-carbethoxy-o-styrylphenylethylamines 2. The key steps were the Bischler–Napieralski reaction to form the isoquinoline unit and photocyclization of the resulting 5-styrylisoquinoline 3 to naphtoisoquinoline 4.

  在这里，我们描述了1,2,3,4-四氢萘并[2,1-的第一全合成˚F ]异喹啉（6）从annoretine Ñ -carbethoxy- ö -styrylphenylethylamines 2。关键步骤是形成异喹啉单元的Bischler-Napieralski反应和所得5-苯乙烯基喹啉3到萘异喹啉4的光环化。
• Synthesis of Chiral Tetrahydro-3-benzazepine Motifs by Iridium-Catalyzed Asymmetric Hydrogenation of Cyclic Ene-carbamates
  作者：Bram B. C. Peters、Pher G. Andersson、Somsak Ruchirawat、Winai Ieawsuwan

  DOI：10.1021/acs.orglett.2c00362

  日期：2022.3.18

  preparation of chiral tetrahydro-3-benzazepine motifs by catalytic asymmetric hydrogenation. Substrates bearing both 1-aryl and 1-alkyl substituents were smoothly converted to the corresponding hydrogenated product with excellent enantioselectivity (91–99% ee) and in isolated yield (92–99%). The synthetic value of this transformation was demonstrated by a gram-scale hydrogenation and application in the syntheses

  提出了一种高效的 N,P 配体铱配合物，用于通过催化不对称氢化简单制备手性四氢-3-苯并氮杂环基序。带有 1-芳基和 1-烷基取代基的底物被顺利地转化为相应的氢化产物，具有优异的对映选择性（91-99% ee）和分离产率（92-99%）。这种转化的合成价值通过克级氢化和在曲匹泮和非诺多泮的合成中的应用得到证实。
• Practical and Metal-Free Electrophilic Aromatic Halogenation by Inter­halogen Compounds Generated In Situ from N-Halosuccinimide and Catalytic TMSCl
  作者：Charnsak Thongsornkleeb、Tapanee Maibunkaew、Jumreang Tummatorn、Anon Bunrit、Somsak Ruchirawat

  DOI：10.1055/s-0034-1378225

  日期：——

  Halomonochloride compounds (ClCl, BrCl, ICl) generated in situ from N-halosuccinimide and catalytic chlorotrimethylsilane (TMSCl, 0.1 equiv) can efficiently halogenate aromatic compounds to give halogenated products in good to excellent yields and selectivities. The reaction can be carried out at room temperature or at lower temperatures, requires only one hour, is practical to apply to a wide range of substrates, and provides a simple access to a variety of haloarene compounds.