3-(6-溴-1,3-苯并二氧戊环-5-基)丙醛 | 57961-87-2

• 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
• 中文名称: 3-(6-溴-1,3-苯并二氧戊环-5-基)丙醛
• 英文名称: 3-(6-bromo-1,3-benzodioxol-5-yl)propanal
• 英文别名: 3-(6-Bromo-benzo[1,3]dioxol-5-YL)-propionaldehyde
• CAS: 57961-87-2
• 化学式: C₁₀H₉BrO₃
• 分子量: 257.084
• InChiKey: LGXSWVDTBSNSPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(6-溴-1,3-苯并二氧戊环-5-基)丙醛 在 2-双环己基膦-2',6'-二甲氧基联苯 、 sodium tetrahydroborate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 caesium carbonate 、 D-脯氨酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 41.5h， 生成 (5aS,8aR)-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydro-1,3-dioxolo[4,5-g]furo[3,4-b]quinolin-6(5aH)-one
  参考文献：
  名称：

  Asymmetric Synthesis of 1-Aza-4-deoxypicropodophyllotoxin

  摘要：

  In our search for new easily accessible analogues based on the natural product podophyllotoxin, we synthesized 1-aza-4-deoxypicropodophyllotoxin in good overall yield and excellent enantioselectivity. The synthesis was centered around a direct asymmetric Mannich reaction using D-proline as the key step for introduction of the chiral centres. Our synthesis of 1-aza-4-deoxypodophyllotoxin was hindered through the increased instability towards epimerization of the C2 position. We did, however, synthesized a new scaffold based on the opened lactone analogue.

  DOI：

  10.1055/s-0033-1338414
• 作为产物：
  描述：

  3,4-methylenedioxy-trans-cinnamic acid 在 lithium aluminium tetrahydride 、 草酰氯 、 硫酸 、 palladium 10% on activated carbon 、 氢气 、 溴 、 二甲基亚砜 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， -78.0~20.0 ℃ 、379.22 kPa 条件下， 反应 28.25h， 生成 3-(6-溴-1,3-苯并二氧戊环-5-基)丙醛
  参考文献：
  名称：

  Asymmetric Synthesis of 1-Aza-4-deoxypicropodophyllotoxin

  摘要：

  In our search for new easily accessible analogues based on the natural product podophyllotoxin, we synthesized 1-aza-4-deoxypicropodophyllotoxin in good overall yield and excellent enantioselectivity. The synthesis was centered around a direct asymmetric Mannich reaction using D-proline as the key step for introduction of the chiral centres. Our synthesis of 1-aza-4-deoxypodophyllotoxin was hindered through the increased instability towards epimerization of the C2 position. We did, however, synthesized a new scaffold based on the opened lactone analogue.

  DOI：

  10.1055/s-0033-1338414

文献信息

• [EN] 1,4-DISUBSTITUTED PIPERIDINE DERIVATIVES AND THEIR USE AS 11-BETAHSD1 INHIBITORS<br/>[FR] DERIVES DE PIPERIDINE 1,4 DISUBSTITUEE ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE 11-BETAHSD1
  申请人：ASTRAZENECA AB

  公开号：WO2004033427A1

  公开（公告）日：2004-04-22

  The use of a compound of formula (I) in the manufacture of a medicament for use in the inhibition of 11βHSD1 is described.

  使用式(I)的化合物制造用于抑制11βHSD1的药物。
• Highly diastereoselective radical cyclisations of chiral sulfinimines
  作者：Elise M. Rochette、William Lewis、Al G. Dossetter、Robert A. Stockman

  DOI：10.1039/c3cc45452e

  日期：——

  Chiral amines are formed by the highly diastereoselective intramolecular addition of alkyl and aryl radicals onto chiral mesityl sulfinimines.

  手性胺是通过烷基和芳基的高度非对映选择性分子内加成到手性异亚磺胺上而形成的。
• Intramolecular Cycloaddition Azomethine Ylides and α-(Trifluoromethyl)styrenes as Dipolarophiles
  作者：Anabel Sánchez Merino、Fernando Rabasa Alcañiz、Daniel Gaviña、Alejandro Delgado、María Sánchez Roselló、Carlos del Pozo

  DOI：10.1002/ejoc.201901098

  日期：2019.10.24

  The intramolecular azomethine ylide cycloaddition of α‐trifluoromethyl styrenes gives rise to the formation of polycyclic fluorinated pyrrolidines. The process takes place in moderate yields and complete diastereoselectivity with the simultaneous generation of up to three stereocenters. Initial attempts of the asymmetric version have been also carried out.

  α-三氟甲基苯乙烯的分子内偶氮甲碱叶立德环加成反应会形成多环氟化吡咯烷。该过程以中等收率和完全非对映选择性进行，同时生成多达三个立体中心。还进行了非对称版本的初步尝试。
• Intramolecular Nitrone Cycloaddition of α-(Trifluoromethyl)styrenes. Role of the CF₃ Group in the Regioselectivity
  作者：Fernando Rabasa-Alcañiz、Amparo Asensio、María Sánchez-Roselló、Marcos Escolano、Carlos del Pozo、Santos Fustero

  DOI：10.1021/acs.joc.6b02880

  日期：2017.3.3

  The intramolecular 1,3-dipolar cycloaddition of ortho-substituted 1,1,1-trifluoromethylstyrene-derived nitrones is described. Tricyclic fused isoxazolidines were obtained as major or exclusive products, in contrast to the case for nonfluorinated substrates, which rendered the bridged derivatives. This change in the regioselectivity was attributed to the electronic and, particularly, steric requirements

  描述了邻位取代的1,1,1-三氟甲基苯乙烯衍生的硝酮的分子内1,3-偶极环加成。与非氟化底物的情况相反，三环稠合的异恶唑烷作为主要或排他性产物获得，非氟化底物形成桥连衍生物。区域选择性的这种变化归因于三氟甲基与甲基相比的电子要求，尤其是空间要求。值得一提的是，三氟甲基苯乙烯首次在1，3-双极性分子内环加成反应中用作亲双性油，从而导致相应的带有季三氟甲基部分的异恶唑烷。最后，
• 1,4-disubstituted piperidine derivatives and their use as 11,betahsd1 inhibitors
  申请人：Barton John Peter

  公开号：US20050256159A1

  公开（公告）日：2005-11-17

  A method for inhibiting 11βHSD1 by administering a compound of formula (I) is described, wherein A, X, Y, R 1 , R 12 , n, q, and m are as described in the specification. Novel compounds and methods employing them are also described and claimed.

  本发明涉及一种通过给予式(I)化合物来抑制11βHSD1的方法，其中A、X、Y、R1、R12、n、q和m如规范中所述。本发明还描述和声明了新的化合物和使用它们的方法。