2-(2-iodo-4,5-methylenedioxyphenyl)ethylamine | 66384-44-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-(2-iodo-4,5-methylenedioxyphenyl)ethylamine
• 英文别名: 2-(2-iodo-4,5-methenodioxyphenyl)ethylamine；2-(6-iodo-benzo[1,3]dioxol-5-yl)-ethylamine；2-iodo-4,5-methylenedioxyphenethyl amine；2-(6-Iodo-1,3-benzodioxol-5-yl)ethanamine
• CAS: 66384-44-9
• 化学式: C₉H₁₀INO₂
• 分子量: 291.088
• InChiKey: LOCDCHYBKIMXMB-UHFFFAOYSA-N

物化性质

• 沸点：
  347.4±42.0 °C(Predicted)
• 密度：
  1.828±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-iodo-4,5-methylenedioxyphenyl)ethylamine 在 盐酸 、 sodium tetrahydroborate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 6.5h， 生成 1-[2-(2-iodo-4,5-methylenedioxyphenyl)ethyl]octahydroindole-7a-carbonitrile
  参考文献：
  名称：

  An Improved Stereocontrolled Route to cis-Erythrinanes by Combined Intramolecular Strecker and Bruylants Reaction

  摘要：

  Condensation of (2-iodophenyl)ethylamines with cyclohexanoylacetaldehyde provided the corresponding aldimines which were reduced yielding secondary phenethylcyclohexanoylethylamines. These in turn were appropriate intermediates to prepare several erythrinanes by a sequential intramolecular Strecker and intramolecular Bruylants reaction. In contrast, the C-ring homologue schelhammeranes were not available on this route.

  DOI：

  10.1007/s00706-004-0184-8
• 作为产物：
  描述：

  1,3-苯并二氧杂环戊烯-5-乙腈 在 硼烷四氢呋喃络合物 、 碘 、 silver trifluoroacetate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.1h， 生成 2-(2-iodo-4,5-methylenedioxyphenyl)ethylamine
  参考文献：
  名称：

  An Improved Stereocontrolled Route to cis-Erythrinanes by Combined Intramolecular Strecker and Bruylants Reaction

  摘要：

  Condensation of (2-iodophenyl)ethylamines with cyclohexanoylacetaldehyde provided the corresponding aldimines which were reduced yielding secondary phenethylcyclohexanoylethylamines. These in turn were appropriate intermediates to prepare several erythrinanes by a sequential intramolecular Strecker and intramolecular Bruylants reaction. In contrast, the C-ring homologue schelhammeranes were not available on this route.

  DOI：

  10.1007/s00706-004-0184-8

文献信息

• Iridium-Catalyzed Asymmetric Intramolecular Allylic Amidation: Enantioselective Synthesis of Chiral Tetrahydroisoquinolines and Saturated Nitrogen Heterocycles
  作者：Johannes F. Teichert、Martín Fañanás-Mastral、Ben L. Feringa

  DOI：10.1002/anie.201006039

  日期：2011.1.17

  For the first time iridium catalysis has been used for the synthesis of chiral tetrahydroisoquinolines with excellent yields and high enantioselectivities (see scheme; cod=1,5‐cyclooctadiene, DBU=1,8‐diazabicyclo[5.4.0]undec‐7‐ene). These products are important chiral building blocks for the synthesis of biologically active compounds, in particular alkaloids.

  首次铱催化已经被用于具有优异的产率和对映选择性高的手性四氢异喹啉的合成（参见流程; COD = 1,5-环辛二烯，DBU = 1,8-二氮杂双环[5.4.0]十一-7-烯）。这些产物是合成生物活性化合物（特别是生物碱）的重要手性结构单元。
• Syntheses of apogalanthamine analogs as .ALPHA.-adrenergic blocking agents. VIII. Syntheses of 4- and 9-bromo-5,6,7,8-tetrahydrodibenz(c,e)azocines and their methylenedioxy derivatives.
  作者：MASARU KIHARA、YOSHIYUKI MIYAKE、MORIO IITOMI、SHIGERU KOBAYASHI

  DOI：10.1248/cpb.33.1260

  日期：——

  The apogalanthamine analogs 4- and 9-bromo-5, 6, 7, 8-tetrahydrodibenz [c, e] azocines (5a and 6a) and their methylenedioxy derivatives (5b and 6b) were prepared by photolysis of the hydrochlorides of the respective N-benzyl-β-phenethylamines (8a, b and 9a, b) substituted with both iodine and bromine atoms. The dibenz [c, e] azocines 6a and 6b were also obtained by thermal syntheses from the biphenyl compounds 17a and 17b, respectively.

  通过光解被碘原子和溴原子取代的 N-苄基-β-苯乙胺（8a, b 和 9a,b）的盐酸盐，制备了 apogalanthamine 类似物 4-和 9-溴-5, 6, 7, 8-四氢二苯并 [c, e] 氮杂环辛（5a 和 6a）及其亚甲二氧基衍生物（5b 和 6b）。通过热合成，还分别从联苯化合物 17a 和 17b 中得到了二苯并 [c, e] 叠氮化合 物 6a 和 6b。
• Enantioselective Highly Efficient Synthesis of (−)-Cephalotaxine Using Two Palladium-Catalyzed Transformations
  作者：Lutz F. Tietze、Hartmut Schirok

  DOI：10.1021/ja991650+

  日期：1999.11.1

  Cephalotaxine (1), the major alkaloid isolated from Cephalotaxus species, has attracted considerable attention due to the promising antitumor activity of several of its derivatives and its unique structural features. Herein we describe a highly efficient enantioselective synthesis of 1 employing two successive Pd-catalyzed transformations starting from 25 to give the pentacyclic product 6. The controlling

  Cephalotaxine (1) 是从 Cephalotaxus 物种中分离出来的主要生物碱，由于其几种衍生物的有希望的抗肿瘤活性及其独特的结构特征而引起了相当大的关注。在本文中，我们描述了 1 的高效对映选择性合成，采用两个连续的 Pd 催化转化，从 25 开始得到五环产物 6。 25 中的控制立体中心是通过对映选择性还原烯酮 16 引入的。
• Sequential Bicyclization to the Skeleton of Lennoxamine and Chilenine Using Pd Catalyst
  作者：Keum Rok Oh、Guncheol Kim

  DOI：10.5012/bkcs.2012.33.12.3933

  日期：2012.12.20

  isolated from Berberis empertrifolia Lam and Berberis darwinii Hook. Although these alkaloids have been known to show weak biological activities, their unique tetracyclic ring system has garnered much attention from synthetic chemists. In the numerous synthetic approaches, the formation of core 7and 5membered rings, actually synthesis of dehydrolennoxamine 3, has been the key target (Figure 1). In this

  具有异吲哚苯并氮杂框架的 Lennoxamine 1 和 chilenine 2 从 Berberis empertrifolia Lam 和 Berberis darwinii Hook 中分离得到。尽管已知这些生物碱具有较弱的生物活性，但其独特的四环环系统已引起合成化学家的广泛关注。在众多合成方法中，核心 7 和 5 元环的形成，实际上是脱氢伦诺沙明 3 的合成，一直是关键目标（图 1）。在本次交流中，我们想为分子提出一种有效的方法，实现正式的合成。已经实现了 3 到 lennoxamine 和 chilenine 的转化。由于直到最近公布的大多数环化方法都是逐步方法，我们希望提出一个从中间体 4 在一个锅中的顺序双环化过程。除了自由基级联反应生成 lennoxamine 1 外，双环化方法很少用于合成 3。预计在用 Pd 处理后，在芳环、酰胺、炔烃官能团上配备碘的分子会发生所需的转化。前体
• Short Synthesis of (−)-Cephalotaxine Using a Radical Cascade
  作者：Tsuyoshi Taniguchi、Hiroyuki Ishibashi

  DOI：10.1021/ol801747m

  日期：2008.9.18

  The short total synthesis of (-)-cephalotaxine is described. The concise construction of the pentacyclic core of this alkaloid was achieved by a radical cascade involving 7-endo and 5-endo cyclizations.

  描述了（-）-头孢他辛的短总合成。该生物碱的五环核的简明结构是通过涉及7-内和5-内环化的自由基级联反应实现的。