3-pentyl-1-octyn-3-ol | 13061-50-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-pentyl-1-octyn-3-ol
• 英文别名: 6-Ethynylundecan-6-ol
• CAS: 13061-50-2
• 化学式: C₁₃H₂₄O
• 分子量: 196.333
• InChiKey: FDSAZYNYLOMTMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-pentyl-1-octyn-3-ol 在 bis-triphenylphosphine-palladium(II) chloride 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 吡啶 、 indium(III) chloride 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 三乙基硼 、 1,2-bis(diphenylphosphino)ethylene 、 sodium methylate 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 2,2-dipentyl-5-vinyl-2,5-dihydrofuran
  参考文献：
  名称：

  Palladium-catalyzed carbon dioxide elimination–fixation reaction of 6-methoxycarbonyloxy-2,4-hexadien-1-ols

  摘要：

  Cyclic carbonates substituted with 1,3-butadienyl moiety were synthesized by a palladium-catalyzed reaction of dienylic carbonates including a carbon dioxide elimination-fixation process. The reaction proceeded via a migration-isomerization of the resulting pi-allyl-palladium intermediates to afford trans-1,3-dienyi-substituted cyclic carbonates in a selective manner. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.010
• 作为产物：
  描述：

  6-Trimethylsilanylethynyl-undecan-6-ol 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以91%的产率得到3-pentyl-1-octyn-3-ol
  参考文献：
  名称：

  Palladium-catalyzed carbon dioxide elimination–fixation reaction of 6-methoxycarbonyloxy-2,4-hexadien-1-ols

  摘要：

  Cyclic carbonates substituted with 1,3-butadienyl moiety were synthesized by a palladium-catalyzed reaction of dienylic carbonates including a carbon dioxide elimination-fixation process. The reaction proceeded via a migration-isomerization of the resulting pi-allyl-palladium intermediates to afford trans-1,3-dienyi-substituted cyclic carbonates in a selective manner. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.010

文献信息

• Divergent Synthesis of Trifluoromethyl Sulfoxides and β-SCF₃ Carbonyl Compounds by Tandem Trifluoromethylthiolation/Rearrangement of Allylic and Propargylic Alcohols
  作者：Deng Zhu、Tong-Mei Ding、Hui-Yun Luo、Hua Ke、Zhi-Min Chen

  DOI：10.1021/acs.orglett.0c02875

  日期：2020.10.2

  A selenium-catalyzed trifluoromethylthiolation/[2,3]-sigmatropic rearrangement of tertiary allylic and propargylic alcohols which could provide straightforward and facile access to trifluoromethyl sulfoxides was developed. Various allylic and allenic trifluoromethyl sulfoxides were obtained with moderate to excellent yields. Meanwhile, a Lewis acid mediated trifluoromethylthiolation/1,2-rearrangement

  开发了硒催化的三烯丙基和丙炔醇的三氟甲基硫醇化/ [2,3]-σ重排，可提供直接而又容易获得的三氟甲基亚砜。获得各种烯丙基和烯丙基三氟甲基亚砜，具有中等至优异的产率。同时，路易斯酸介导的trifluoromethylthiolation / 1,2-重排合成β-SCF 3的羰基化合物也已实现。这两个串联反应的特征是反应条件温和且不含金属。在这两个反应中，揭示了亲电三氟甲基硫醇化的化学选择性。
• Palladium‐Catalyzed Cascade Carbonylation to α,β‐Unsaturated Piperidones via Selective Cleavage of Carbon–Carbon Triple Bonds
  作者：Yao Ge、Fei Ye、Ji Yang、Anke Spannenberg、Haijun Jiao、Ralf Jackstell、Matthias Beller

  DOI：10.1002/anie.202108120

  日期：2021.10.4

  A direct and selective synthesis of α,β-unsaturated piperidones by a new palladium-catalyzed cascade carbonylation is described. In the presented protocol, easily available propargylic alcohols react with aliphatic amines to provide a broad variety of interesting heterocycles. Key to the success of this transformation is a remarkable catalytic cleavage of the present carbon–carbon triple bond by using

  描述了通过新型钯催化级联羰基化直接选择性合成 α,β-不饱和哌啶酮。在所提出的方案中，容易获得的炔丙醇与脂肪胺反应，提供多种有趣的杂环。这种转化成功的关键是通过使用以 2-二苯基膦吡啶为配体的特定催化剂和适当的反应条件，对现有的碳-碳三键进行显着的催化裂解。机理研究和控制实验表明支链不饱和酸11是关键的中间体。
• 6-(BIPHENYL-ESTER)-3H-NAPHTHO[2,1-B]PYRANS AS PHOTOCHROMIC DICHROIC DYES AND OPTICAL ARTICLE CONTAINING THEM
  申请人：Aiken Stuart

  公开号：US20100039688A1

  公开（公告）日：2010-02-18

  A naphthopyran compound represented by the formula (I) wherein: n 1 , n 2 , p, m and q represent an integer; R 1 , R 2 and R 4 , represent a group selected from halogen, —R a , —OH, —OR a , —SH, —SR a , —NH 2 , —NR a R a1 , —NR b R c , —CO—R a , —CO 2 R a1 , —OC(O)—R d , —X—(R e )—Y, linear or branched (C 1 -C 18 ) perfluoroalkyl group, wherein R a , R a1 , R b , R c , X, Y, R e , and R d are as defined in the description; Z represents a group selected from CO, CS, SO, SO 2 , CO 2 , C(O)S, CS 2 , C(O)NH, C(O)NR a , C(S)NH, C(S)NR a and C═NR a ; R 3 represents a group selected from halogen, —R a , linear or branched (C 1-18 ) perfluoroalkyl group —OH, —OR a , —SH, —SR a , —NH 2 , and —NR a R a1 ; R 6 represents a group selected from —R a which may be optionally substituted, linear or branched (C 1-18 ) perfluoroalkyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl, which may be optionally substituted; R 5 represents a group selected from: halogen, —R a , linear or branched (C 1-18 ) perfluoroalkyl group, —OH, —OR a , —SH, —SR a , —NH 2 , —NR a R a1 , —CO—R a , —O—C(O)—R a and —CO 2 R a1 ; or when q is equal to 2, then two R 5 together represents further a group —O—(CH 2 ) q1 —O— wherein q 1 represents an integer comprised from 1 to 3 inclusive.

  一种萘吡喃化合物，其化学式为（I），其中：n1、n2、p、m和q表示整数；R1、R2和R4表示从卤素、—Ra、—OH、—ORa、—SH、—SRa、—NH2、—NRaRa1、—NRbRc、—CO—Ra、— Ra1、—OC(O)—Rd、—X—(Re)—Y、线性或支链（C1-C18）全氟烷基组中选择的一个基团，其中Ra、Ra1、Rb、Rc、X、Y、Re和Rd如描述中所定义；Z表示从CO、CS、SO、SO2、CO2、C(O)S、CS2、C(O)NH、C(O)NRa、C(S)NH、C(S)NRa和C═NRa中选择的一个基团；R3表示从卤素、—Ra、线性或支链（C1-18）全氟烷基组、—OH、—ORa、—SH、—SRa、—NH2和—NRaRa1中选择的一个基团；R6表示从可选择替代的—Ra、线性或支链（C1-18）全氟烷基、环烷基、杂环烷基、芳基和杂芳基中选择的一个基团；R5表示从卤素、—Ra、线性或支链（C1-18）全氟烷基组、—OH、—ORa、—SH、—SRa、—NH2、—NRaRa1、—CO—Ra、—O—C(O)—Ra和— Ra1中选择的一个基团；或者当q等于2时，那么两个R5一起进一步表示一个基团—O—(CH2)q1—O—，其中q1表示从1到3的整数。
• Synthesis process
  申请人：Begley J. William

  公开号：US20060025617A1

  公开（公告）日：2006-02-02

  A process for synthesizing a single isomer of a naphthacene compound comprises the steps of: (a) reacting a symmetrically substituted 1,1-diarylpropargyl alcohol compound with a reagent capable of forming a leaving group to form a reaction mixture containing a intermediate; and then (b) heating the intermediate in the presence of a solvent and in the absence of any oxidizing agent to form a single naphthacene compound.

  合成单异构体萘并芘化合物的过程包括以下步骤：(a)将对称取代的1,1-二芳基丙炔醇化合物与能够形成离去基的试剂反应，形成包含中间体的反应混合物；然后(b)在溶剂存在且无氧化剂存在的情况下加热该中间体，形成单一的萘并芘化合物。
• 3H-NAPHTH0 [2,1-B] PYRANS AS PHOTOCHROMIC DICHROIC DYES AND OPTICAL ARTICLE CONTAINING THEM
  申请人：Aiken Stuart

  公开号：US20100202033A1

  公开（公告）日：2010-08-12

  A naphthopyran compound represented by the formula (I): wherein: n 1 , n 2 , p, q is an integer comprised from 0 to 5 inclusive; m is an integer comprised from 0 to 4 inclusive; R 1 and R 2 represent a group selected from halogen, —R a , —OH, —OR a , —SH, —SR a , —NH 2 , —NR a R a1 , —NR b R c , —CO—R a , and —CO 2 R a1 , wherein R a , R a1 , R b and R c , are as defined in the description; R 3 represents a group selected from halogen, —R a , —OH, —OR a , —SH, —SR a , —NH 2 , and —NR a R a1 ; R 4 represents a group selected from halogen, —R a , —OH, —OR a , —SH, —SR a , —NH 2 , —NR a R a1 , —CO—R a , and —CO 2 R a1 ; R 5 represents a group selected from: halogen, —R a , —OH, —OR a , —SH, —SR a , —NH 2 , and —NR a R a1 , wherein R a and R a1 are as defined hereinbefore, or when q is equal to 2, then two R 5 together represent further a group —O—(CH 2 ) q1 —O— wherein q1 represents an integer comprised from 1 to 3 inclusive.

  一种萘并吡喃化合物，其化学式表示为（I）：其中：n1、n2、p、q为0至5之间的整数；m为0至4之间的整数；R1和R2表示从卤素，—Ra，—OH，—ORa，—SH，—SRa，—NH2，—NRaRa1，—NRbRc，—CO—Ra和—CO2Ra1中选择的基团，其中Ra，Ra1，Rb和Rc如上所述；R3表示从卤素，—Ra，—OH，—ORa，—SH，—SRa，—NH2和—NRaRa1中选择的基团；R4表示从卤素，—Ra，—OH，—ORa，—SH，—SRa，—NH2，—NRaRa1，—CO—Ra和—CO2Ra1中选择的基团；R5表示从卤素，—Ra，—OH，—ORa，—SH，—SRa，—NH2和—NRaRa1中选择的基团，其中Ra和Ra1如上所述，或者当q等于2时，两个R5共同表示进一步的基团—O—（CH2）q1—O—，其中q1为1至3之间的整数。