1-pentynyldimethylalane | 77102-19-3

• 分子结构分类: 有机化合物 - 乙炔化物 - 金属乙炔化物
• 英文名称: 1-pentynyldimethylalane
• 英文别名: dimethylaluminum 1-pentynide；Dimethyl(pent-1-yn-1-yl)alumane；dimethyl(pent-1-ynyl)alumane
• CAS: 77102-19-3
• 化学式: C₇H₁₃Al
• 分子量: 124.162
• InChiKey: TZHIJSSJDNNMHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-pentynyldimethylalane 在 palladium on activated charcoal 盐酸 、 三氟甲磺酸三甲基硅酯 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 13.75h， 生成 (R)-2-pentylpiperidine hydrochloride
  参考文献：
  名称：

  Asymmetric α-Alkynylation of Piperidine via N-Sulfinyliminium Salts

  摘要：

  Piperidine was stereoselectively alpha-alkynylated in a four-step sequence made up of transformation to a chiral nonracemic N-sulfinylpiperidine, anodic oxidation to N-sulfinyliminium ion equivalent, alkynylation through addition of a mixed organoaluminum derivative, and final acidic deprotection of the sulfoxide. Overall yields are around 50%, and the diastereoselectivity of the nucleophilc addition was between 92 and 99% de, allowing isolation of the final product with 99% enantiomeric purity.

  DOI：

  10.1021/jo070631c
• 作为产物：
  描述：

  1-戊炔 、 正丁基锂 、 三甲基铝 、 正己烷 、 三氯化铝 、 苯 生成 1-pentynyldimethylalane
  参考文献：
  名称：

  NEGISHI, EI-ICHI;VAN, HORN, D. E.;YOSHIDA, TADAO, J. AMER. CHEM. SOC., 1985, 107, N 23, 6639-6647

  摘要：

  DOI：

文献信息

• Room Temperature Lewis Base-Catalyzed Alumination of Terminal Alkynes
  作者：Yuhan Zhou、Thomas Lecourt、Laurent Micouin

  DOI：10.1002/adsc.200900414

  日期：2009.11

  An efficient and mild access to mixed dimethylalkynylaluminum reagents has been developed via a direct Lewis base-catalyzed alumination of terminal alkynes by trimethylaluminum. The use of bis(trimethylsilyl)methylamine enables the metalation at room temperature with only 1% of catalyst loading.

  到混合dimethylalkynylaluminum试剂的有效和温和的访问已被开发经由末端炔烃的通过三甲基直接路易斯碱催化的脱铝。使用双（三甲基甲硅烷基）甲胺能够在室温下以仅1％的催化剂负载量进行金属化。
• Controlled carbometalation. 20. Carbometalation reaction of alkynes with organoalene-zirconocene derivatives as a route to stereo-and regiodefined trisubstituted alkenes
  作者：Eiichi Negishi、David E. Van Horn、Tadao Yoshida

  DOI：10.1021/ja00309a036

  日期：1985.11
• Direct Synthesis of Polysubstituted Aluminoisoxazoles and Pyrazoles by a Metalative Cyclization
  作者：Olivier Jackowski、Thomas Lecourt、Laurent Micouin

  DOI：10.1021/ol202389u

  日期：2011.10.21

  Alumino-heteroles are obtained from simple precursors in a fully chemo- and regioselective manner by a metalative cyclization. The carbon-aluminum bond is still able to react further with several electrophiles, without the need of transmetalation. This synthetic route provides a novel entry to heterocyclic organoaluminum reagents as well as a straightforward access to 3,4,5-trisubstituted isoxazoles and 1,3,4,5-tetrasubstituted pyrazoles.
• Organoaluminum-induced opening of the pyranosidic ring of benzyl 2-deoxy-2-C-methylpentopyranosides
  作者：Tord Inghardt、Torbjoern Frejd

  DOI：10.1021/jo00284a028

  日期：1989.11
• INGHARDT, TORD;FREJD, TORBJORN, J. ORG. CHEM., 54,(1989) N3, C. 5539-5543
  作者：INGHARDT, TORD、FREJD, TORBJORN

  DOI：——

  日期：——