2-(2-(3-methoxyphenyl)allyl)isoindoline-1,3-dione | 85278-39-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(2-(3-methoxyphenyl)allyl)isoindoline-1,3-dione
• 英文别名: 2-(3-methoxyphenyl)-3-phthalimido-1-propene；2-(3'-methoxy)phenyl-3-phthalimidopropene；2-[2-(3-Methoxyphenyl)prop-2-enyl]isoindole-1,3-dione
• CAS: 85278-39-3
• 化学式: C₁₈H₁₅NO₃
• 分子量: 293.322
• InChiKey: WRIJYZVQTXMFHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-(3-methoxyphenyl)allyl)isoindoline-1,3-dione 在 4-二甲氨基吡啶 、 hydrazine hydrate 、 三乙胺 、 rose bengal 作用下， 以 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 40.0h， 生成 5-(3-methoxyphenyl)-5-neopentyl-2-phenyl-4,5-dihydrooxazole
  参考文献：
  名称：

  烯丙基酰胺与 N-羟基邻苯二甲酰亚胺酯的可见光促进自由基烷基化/环化：恶唑啉的合成

  摘要：

  开发了一种高效的光催化烯丙基酰胺与N-羟基邻苯二甲酰亚胺酯的烷基化/环化反应。该转化利用烷基自由基攻击烯丙基酰胺，并辅以廉价的玫瑰红作为光催化剂，以中等至优异的产率制备一系列烷基取代的恶唑啉。区域选择性高、操作安全、条件温和、底物通用性好，使该协议具有广阔的应用前景。

  DOI：

  10.1016/j.cclet.2021.09.067
• 作为产物：
  描述：

  3-甲氧基苯乙酮 在 N-溴代丁二酰亚胺(NBS) 、 potassium tert-butylate 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.45h， 生成 2-(2-(3-methoxyphenyl)allyl)isoindoline-1,3-dione
  参考文献：
  名称：

  烯丙基酰胺与 N-羟基邻苯二甲酰亚胺酯的可见光促进自由基烷基化/环化：恶唑啉的合成

  摘要：

  开发了一种高效的光催化烯丙基酰胺与N-羟基邻苯二甲酰亚胺酯的烷基化/环化反应。该转化利用烷基自由基攻击烯丙基酰胺，并辅以廉价的玫瑰红作为光催化剂，以中等至优异的产率制备一系列烷基取代的恶唑啉。区域选择性高、操作安全、条件温和、底物通用性好，使该协议具有广阔的应用前景。

  DOI：

  10.1016/j.cclet.2021.09.067

文献信息

• Highly Enantioselective Iridium-Catalyzed Hydrogenation of 2-Aryl Allyl Phthalimides
  作者：Albert Cabré、Elia Romagnoli、Pol Martínez-Balart、Xavier Verdaguer、Antoni Riera

  DOI：10.1021/acs.orglett.9b03865

  日期：2019.12.6

  The iridium-catalyzed asymmetric hydrogenation of 2-aryl allyl phthalimides to afford enantioenriched β-aryl-β-methyl amines is presented. Recently developed Ir-MaxPHOX catalysts are used for this enantioselective transformation. The mild reaction conditions and the feasible removal of the phthalimido group makes this catalytic method easily scalable and of great interest to afford chiral amines. The

  提出了铱催化的2-芳基烯丙基邻苯二甲酰亚胺的不对称氢化，以提供对映体富集的β-芳基-β-甲基胺。最近开发的Ir-MaxPHOX催化剂用于该对映选择性转化。温和的反应条件和邻苯二甲酰亚胺基团的可行去除使得该催化方法易于扩展，并且对于提供手性胺具有极大的兴趣。（R）-酪蛋白，OTS514和对映体富集的3-甲基二氢吲哚的正式合成例证了这种新方法的重要性。
• Allyl amine MAO inhibitors
  申请人：Merrell Toraude et Compagnie

  公开号：US04454158A1

  公开（公告）日：1984-06-12

  Compounds of the formula ##STR1## wherein: R is phenyl, phenyl monosubstituted, disubstituted, or trisubstituted by (C.sub.1 -C.sub.8) alkyl, (C.sub.1 -C.sub.8)alkoxy, hydroxy, chlorine, bromine, iodine, fluorine, trifluoromethyl, nitro, (C.sub.1 -C.sub.6)alkylcarbonyl, benzoyl, or phenyl; 1-, or 2-naphthyl; 1-, 2-, or 3-indenyl; 1-, 2-, or 9-fluorenyl; 1-, 2-, or 3-piperidinyl; 2- or 3-pyrrolyl; 2- or 3-thienyl; 2- or 3-furanyl; 2- or 3- indolyl; 2- or 3-thianaphthenyl; or 2- or 3-benzofuranyl; R.sub.1 is hydrogen, (C.sub.1 -C.sub.8)alkyl, benzyl, or phenethyl; X and Y independently, are hydrogen, fluorine, chlorine, or bromine; and A is a divalent radical of the formula: ##STR2## wherein R.sub.2 is hydrogen, methyl, or ethyl, and m and n, independently, are an integer from 0 to 4, provided that m+n cannot be greater than 4; --(CH.sub.2).sub.p --D--(CH.sub.2).sub.q --, wherein D is oxygen, or sulfur, p is an integer from 2 to 4, and q is an integer from 0 to 2, provided that p+q cannot be greater than 4; or --(CH.sub.2).sub.r CH.dbd.CH(CH.sub.2).sub.s --, wherein r is an integer from 1 to 3 and s is an integer from 0 to 2, provided that r+s cannot be greater than 3; or a non-toxic, pharmaceutically-acceptable acid addition salt thereof; provided that when each of X and Y in Formula I is hydrogen, R cannot be phenyl; are MAO inhibitors useful for treating depression. Processes and intermediates for preparing the compounds of Formula I or II are also described.

  公式为##STR1##的化合物，其中：R是苯基，苯基单取代，双取代或三取代，取代基为(C.sub.1-C.sub.8)烷基，(C.sub.1-C.sub.8)氧烷基，羟基，氯，溴，碘，氟，三氟甲基，硝基，(C.sub.1-C.sub.6)烷基羰基，苯甲酰基或苯基；1-，或2-萘基；1-，2-，或3-茚基；1-，2-，或9-芴基；1-，2-，或3-哌啶基；2-或3-吡咯基；2-或3-噻吩基；2-或3-呋喃基；2-或3-吲哚基；2-或3-噻萘基；或2-或3-苯并呋喃基；R.sub.1是氢，(C.sub.1-C.sub.8)烷基，苄基或苯乙基；X和Y独立地是氢，氟，氯或溴；A是公式的双价基团：##STR2##其中R.sub.2是氢，甲基或乙基，m和n独立地是从0到4的整数，但m+n不能大于4；--(CH.sub.2).sub.p --D--(CH.sub.2).sub.q --，其中D是氧或硫，p是从2到4的整数，q是从0到2的整数，但p+q不能大于4；或--(CH.sub.2).sub.r CH.dbd.CH(CH.sub.2).sub.s --，其中r是从1到3的整数，s是从0到2的整数，但r+s不能大于3；或其非毒性、药学上可接受的酸盐；在公式I中的X和Y中每个都是氢时，R不能是苯基；这些是用于治疗抑郁症的MAO抑制剂。还描述了制备公式I或II化合物的过程和中间体。
• A Catalytic Asymmetric Chlorocyclization of Unsaturated Amides
  作者：Arvind Jaganathan、Atefeh Garzan、Daniel C. Whitehead、Richard J. Staples、Babak Borhan

  DOI：10.1002/anie.201006910

  日期：2011.3.7

  The asymmetric chlorocyclization of unsaturated amides catalyzed by (DHQD)2PHAL yields oxazoline and dihydrooxazine derivatives (see scheme). The reaction is operationally simple and employs 1–2 mol % of the commercially available (DHQD)2PHAL (hydroquinidine 1,4‐phthalazinediyl diether) catalyst. Different substitution patterns of the olefin as well as aromatic and aliphatic olefin substituents are

  （DHQD）2 PHAL催化不饱和酰胺的不对称氯环化反应，生成恶唑啉和二氢恶嗪衍生物（参见方案）。该反应操作简单，并使用1-2 mol％的市售（DHQD）2 PHAL（氢奎尼丁1,4-萘二甲酰二醚）催化剂。烯烃以及芳族和脂族烯烃取代基的不同取代方式具有良好的耐受性。DCDPH = N，N-二氯-5,5-二苯基乙内酰脲。
• Characterization of a Series of 3-Amino-2-phenylpropene Derivatives as Novel Bovine Chromaffin Vesicular Monoamine Transporter Inhibitors
  作者：Rohan P. Perera、D. Shyamali Wimalasena、Kandatege Wimalasena

  DOI：10.1021/jm030004p

  日期：2003.6.1

  A series of 3-amino-2-phenylpropene (APP) derivatives have been synthesized and characterized as novel competitive inhibitors, with K-i values in the muM range, for the bovine chromaffin granule membrane monoamine transporter(s) (bVMAT). Although, these inhibitors are structurally similar to the bVMAT substrate tyramine, none of them were measurably transported into the granule. Structure-activity studies have revealed that, while the 3'- or 4'-OH groups on the aromatic ring enhance the inhibition potency, Me or OMe groups in these positions reduce the inhibition potency. Halogen substitution on the 4'-position of the aromatic ring causes gradual increase of the inhibition potency parallel to the electron donor ability of the halogen. Substituents on the NH2 as well as on the 3-position of the alkyl chain reduce the inhibition potency. Comparative structure-activity analyses of APP derivatives with tyramine and the neurotoxin 1-methyl-4-phenylpyridinium suggest that the flexibility of the side chain and the relative orientation of the NH2 group may be critical for the efficient transport of the substrate through the bVMAT. Comparable bVMAT affinities of these inhibitors to that of DA and other pharmacologically active amines suggest that they are suitable for the structure-activity and mechanistic studies of monoamine transporters and may also be useful in modeling the mechanism of action of amphetamine-related derivatives.
• US4454158A
  申请人：——

  公开号：US4454158A

  公开（公告）日：1984-06-12