9-undecynal

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-undecynal
• 英文别名: Undec-9-ynal
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: RSZPXTHYSHYJBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-undecynal 在 Lindlar's catalyst 喹啉 、 Tris(t-butoxy)(2,2-dimethylpropylidyne)tungsten(VI), 98% Schrock Alkyne Metathesis Catalyst 、 重铬酸吡啶 、 氢气 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 20.0~80.0 ℃ 、101.33 kPa 条件下， 反应 28.5h， 生成 灵猫酮
  参考文献：
  名称：

  Ring closing alkyne metathesis: stereoselective synthesis of civetone

  摘要：

  A concise and stereoselective synthesis of the macrocyclic musk civetone 6 is reported starting from readily available 9-undecynol. The key steps comprise a ring closing metathesis of diyne 4 followed by Lindlar reduction of the resulting cycloalkyne 5. The cyclization can be effected either by using catalytic amounts of the Schrock alkylidyne complex (t-BuO)(3)W drop CCMe3 or by means of an in situ catalyst mixture generated from Mo(CO)(6) and p-trifluoromethylphenol. Both catalyst systems turned out to be compatible with the unprotected ketone function of the substrate. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(00)00096-6
• 作为产物：
  描述：

  9-十一炔酸 在 盐酸 、 三(五氟苯基)硼烷 、 水 作用下， 以 四氢呋喃 、 氘代苯 为溶剂， 反应 5.0h， 生成 9-undecynal
  参考文献：
  名称：

  Selective Reduction of Carboxylic Acids to Aldehydes Catalyzed by B(C₆F₅)₃

  摘要：

  B(C6F5)(3) efficiently catalyzes hydrosilylation of aliphatic and aromatic carboxylic acids to produce disilyl acetals under mild conditions. Catalyst loadings can be as low as 0.05 mol %, and bulky tertiary silanes are favored to give selectively the acetals. Acidic workup of the disilyl acetals results in the formation of aldehydes in good to excellent yields.

  DOI：

  10.1021/ol303296a

文献信息

• Pronounced anti-proliferative activity and tumor cell selectivity of 5-alkyl-2-amino-3-methylcarboxylate thiophenes
  作者：Joice Thomas、Alenka Jecic、Els Vanstreels、Lizette van Berckelaer、Romeo Romagnoli、Wim Dehaen、Sandra Liekens、Jan Balzarini

  DOI：10.1016/j.ejmech.2017.03.044

  日期：2017.5

  mid-nanomolar range with 500- to 1000-fold tumor cell selectivity. The compounds preferentially inhibited the proliferation of T-lymphoma CEM and Molt/4, prostate PC-3, kidney Caki-1 and hepatoma Huh-7 tumor cells, but were virtually inactive against other tumor cell lines including B-lymphoma Raji and cervix carcinoma HeLa cells. The novel prototype drug 3j (containing a 5-heptyl chain) elicited a cytotoxic

  5-（2-（4-甲氧基苯基）乙基）-2-氨基-3-甲基羧酸噻吩（TR560）是最近发现的新型肿瘤选择性化合物的原型药物，该化合物优先抑制特定肿瘤细胞类型的增殖（例如白血病/淋巴瘤）。在这里，我们通过用烷基链取代4-甲氧基苯基部分来简化分子，从而进一步提高了肿瘤的选择性。几种在C-5处含有至少6个（己基）至9个（壬基）碳单元的烷基的2-氨基-3-甲基羧酸盐噻吩衍生物在500-1000的中纳摩尔范围内表现出显着的抗增殖活性。倍的肿瘤细胞选择性。这些化合物优先抑制T淋巴瘤CEM和Molt / 4，前列腺PC-3，肾Caki-1和肝癌Huh-7肿瘤细胞的增殖，但实际上对其他肿瘤细胞系（包括B淋巴瘤Raji和宫颈癌HeLa细胞）无活性。新型原型药物3j（包含5-庚基链）已在暴露4小时后引起细胞毒性而不是细胞抑制活性。异常的肿瘤选择性无法通过敏感肿瘤细胞与耐药肿瘤细胞对药物的差异吸收（或外排）来解释。
• Photo-organocatalytic synthesis of acetals from aldehydes
  作者：Nikolaos F. Nikitas、Ierasia Triandafillidi、Christoforos G. Kokotos

  DOI：10.1039/c8gc03605e

  日期：——

  developed. Utilizing thioxanthenone as the photocatalyst and inexpensive household lamps as the light source, a variety of aromatic and aliphatic aldehydes have been converted into acyclic and cyclic acetals in high yields. The reaction mechanism was extensively studied.

  已经开发出用于醛的高效缩醛化的温和绿色光有机催化方案。利用噻吨酮作为光催化剂，使用廉价的家用灯作为光源，已将各种芳族和脂族醛高产率地转化为无环和环状缩醛。反应机理得到了广泛的研究。
• Photochemical Hydroacylation of Michael Acceptors Utilizing an Aldehyde as Photoinitiator
  作者：Ioanna K. Sideri、Errika Voutyritsa、Christoforos G. Kokotos

  DOI：10.1002/cssc.201901725

  日期：2019.9.20

  leading to good yields, and mechanistic experiments were performed to elucidate the catalyst's possible mechanistic pathway. Moreover, the inherent selectivity challenge regarding α,α-disubstituted aldehydes (decarbonylation problem) was studied and addressed.

  迈克尔受体的加氢酰化是形成新CC键的有用工具。在这项工作中，开发了一种环境友好的程序，利用4-氰基苯甲醛作为光引发剂，家用灯泡作为辐照源。各种各样的底物都具有良好的耐受性，从而导致了高收率，并且进行了机理实验以阐明催化剂的可能机理。此外，研究和解决了有关α，α-二取代醛的固有选择性挑战（脱羰问题）。
• Enantioselective Organocatalytic Synthesis of 2-Oxopiperazines from Aldehydes: Identification of the Elusive Epoxy Lactone Intermediate
  作者：Nikolaos Kaplaneris、Constantinos Spyropoulos、Maroula G. Kokotou、Christoforos G. Kokotos

  DOI：10.1021/acs.orglett.6b02699

  日期：2016.11.18

  organocatalytic linchpin catalysis approach was envisaged to convert simple aldehydes into enantioenriched 2-oxopiperazines. A four-step reaction sequence (chlorination, oxidation, substitution, and cyclization) was developed and led to different substitution patterns in high yields and selectivities. The reaction mechanism was studied, and the previously elusive epoxy lactone intermediate was identified by

  设想了一种有机催化的关键催化方法，将简单的醛转化为对映体富集的2-氧代哌嗪。开发了四步反应序列（氯化，氧化，取代和环化），并以高收率和选择性导致了不同的取代方式。研究了反应机理，并通过HRMS鉴定了以前难以捉摸的环氧内酯中间体。
• CARBOHYDRATE-BASED SURFACTANTS
  申请人：THE ARIZONA BOARD OF REGENTS ON BEHALF OF THE UNIVERSITY OF ARIZONA

  公开号：US20170121362A1

  公开（公告）日：2017-05-04

  The present invention provides carbohydrate-based surfactants and methods for producing the same. Methods for producing carbohydrate-based surfactants include using a glycosylation promoter to link a carbohydrate or its derivative to a hydrophobic compound.