2-Methylenheptandisaeure-diethylester | 34762-19-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-Methylenheptandisaeure-diethylester
• 英文别名: diethyl α-methylene pimelate；diethyl 2-methyleneheptanedioate；ethyl 6-carbethoxyhept-6-enoate；2-methylene-heptanedioic acid diethyl ester；2-Methylen-heptandisaeure-diaethylester；Heptanedioic acid, 2-methylene-, diethyl ester；diethyl 2-methylideneheptanedioate
• CAS: 34762-19-1
• 化学式: C₁₂H₂₀O₄
• 分子量: 228.288
• InChiKey: PNSRVQKIEKYGPJ-UHFFFAOYSA-N

物化性质

• 沸点：
  94-98 °C(Press: 0.15 Torr)
• 密度：
  0.999±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Methylenheptandisaeure-diethylester 在 四丁基硫酸氢铵 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 60.0h， 生成 Ethyl 2-diethoxyphosphoryl-3-oxocycloheptane-1-carboxylate
  参考文献：
  名称：

  First synthesis of (±)-bis-homosarkomycin ethyl ester

  摘要：

  A five step synthesis of (+/-)-bis-homosarkomycin ethyl ester 6 has been achieved starting from commercially available ethyl phosphonoacetate and ethyl 5-bromovalerate. The Successful synthetic approach to 6 uses alpha-methylene pimelate 3 as a key intermediate. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.079
• 作为产物：
  描述：

  5-溴戊酸乙酯 在 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 23.0h， 生成 2-Methylenheptandisaeure-diethylester
  参考文献：
  名称：

  The enantioselective synthesis of tetracyclic methyllycaconitine analogues

  摘要：

  A new enantioselective synthesis of ABEF ring analogues of methyllycaconitine has been developed using a chiral cobalt(III) salen-catalyzed Diels-Alder reaction to form the B ring. Subsequent elaboration to form the A, E and F rings was achieved by sequential Dieckmann, Mannich and Wacker-type cyclizations to afford tetracyclic analogues in 97.5% ee. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.026

文献信息

• Nickel-Catalyzed Preparations of Functionalized Organozincs
  作者：Stephan Vettel、Andrea Vaupel、Paul Knochel

  DOI：10.1021/jo960808v

  日期：1996.1.1

  (X = Br, Cl) via a halogen-zinc exchange reaction. The treatment of terminal alkenes with diethylzinc (neat, 25-60 degrees C) in the presence of Ni(acac)(2) as a catalyst (1-5 mol %) and 1,5-cyclooctadiene (COD) affords the corresponding dialkylzincs via a hydrozincation reaction. Whereas the conversion for simple alkenes bearing a remote functionality reaches 40 to 63%, the hydrozincation of allylic

  在Ni（acac）（2）（5 mol％）存在下，伯烷基溴化物或氯化物与二乙基锌的反应通过卤素-锌交换反应提供了相应的烷基卤化锌（X = Br，Cl）。在Ni（acac）（2）作为催化剂（1-5 mol％）和1,5-环辛二烯（COD）的存在下用二乙基锌（纯净的25-60摄氏度）处理末端烯烃。得到相应的二烷基锌通过氢化锌反应。带有少量官能团的简单烯烃的转化率达到40％到63％，而烯丙基，均烯丙基醇和烯丙基胺的加氢锌反应非常有效（转化率为85-95％）。用CuCN.2LiCl进行金属转移后，所有获得的有机金属锌与各种亲电试剂（烯丙基卤，烯酮，酰氯，炔基卤，丙酸乙酯）反应。
• Synthesis of Erythrina and Related Alkaloids. XXVIII. Studies toward Total Synthesis of Non-aromatic Erythrina Alkaloids. (1). Synthesis and Isomerization of Unsaturated Bicyclic .DELTA.-Lactones.
  作者：Yoshisuke TSUDA、Akiko ISHIURA、Saho TAKAMURA、Shinzo HOSOI、Kimiaki ISOBE、Kunihiko MOHRI

  DOI：10.1248/cpb.39.2797

  日期：——

  As a model of the C/D ring system of erythroidines, bicyclic unsaturated δ-lactones were synthesized in a regio-selective manner, and their isomerization reaction in the presence of acid, base (DBU, 1, 8-diazabicyclo[5.4.0]undec-7-ene), and NaOH were studied. In the lactone form, the 6-ene (3) was the most unstable and isomerized to the 5-ene (1) then to the 1(6)-ene (2). The latter two lactones equilibrate to give ca. 3 : 2 mixture of 1 and 2 in the presence of DBU. On the contrary, in the opened form (NaOH), the lactone 1 was the most unstable and isomerized to 2 and 3. The 1(10)-ene (4) was inert under all of the conditions examined.

  作为红细胞素C/D环系统的模型，合成了环状不饱和δ-内酯，并研究了它们在酸、碱（DBU，1, 8-二氮双环[5.4.0]十一烯）和氢氧化钠存在下的异构化反应。在内酯形式中，6-烯（3）是最不稳定的，并异构化为5-烯（1），然后再转变为1(6)-烯（2）。后两种内酯在DBU的存在下达到了大约3:2的1和2的平衡。相反，在打开状态下（氢氧化钠），内酯1是最不稳定的，异构化为2和3。1(10)-烯（4）在所有检查的条件下都表现惰性。
• The Grob/Eschenmoser fragmentation of cycloalkanones bearing β-electron withdrawing groups: a general strategy to acyclic synthetic intermediates
  作者：Judith Hierold、Tina Hsia、David W. Lupton

  DOI：10.1039/c0ob00632g

  日期：——

  a β-electron withdrawing group to cycloalkanones allows facile C–C bond fragmentation. The reaction has been demonstrated with a large range of ring sizes, bearing various leaving and electron withdrawing groups, and using a variety of nitrogen and oxygen containing nucleophiles (>30 examples). The application of fragmentation products to the preparation of substituted γ-lactones has been demonstrated

  在环烷酮中引入一个β电子吸电子基团可以使CC键断裂变得容易。已经证明该反应具有大范围的环尺寸，带有各种离去和吸电子基团，并使用了各种含氮和氧的亲核试剂（> 30个实例）。已经证明了碎裂产物在制备取代的γ-内酯中的应用。据报道，机理研究提示了Grob / Eschenmoser型反应。
• Preparation of alkylzinc bromides using a new Mn/Cu catalyzed bromine-zinc exchange reaction
  作者：Ingo Klement、Paul Knochel、Khi Chau、Gérard Cahiez

  DOI：10.1016/0040-4039(94)88017-4

  日期：1994.2

  The reaction of functionalized primary alkyl bromides with Et2Zn in DMPU in the presence of a catalytic mixed metal system constituted of MnBr2 (or FeCl3) and CuCl provides functionalyzed alkylzinc bromides (> 80 % yield). In the presence of PdCl2(dppf) or CuCN·2LiCl, these organozinc species reach with a range of electrophiles providing various polyfunctional molecules in good yields.

  在由MnBr 2（或FeCl 3）和CuCl组成的催化混合金属体系存在下，官能化的伯烷基溴化物与Et 2 Zn在DMPU中的反应提供了官能化的烷基锌溴化物（收率> 80％）。在PdCl 2（dppf）或CuCN·2LiCl的存在下，这些有机锌物质会与一系列亲电试剂接触，从而以良好的收率提供各种多官能分子。
• Modulators of cystic fibrosis transmembrane conductance regulator, pharmaceutical compositions, methods of treatment, and process for making the modulators
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US11066417B2

  公开（公告）日：2021-07-20

  Compounds of Formula (I): pharmaceutically acceptable salts thereof, deuterated derivatives of any of the foregoing, and metabolites of any of the foregoing are disclosed. Pharmaceutical compositions comprising the same, methods of treating cystic fibrosis using the same, and methods for making the same are also disclosed.

  式 (I) 的化合物： 公开了前述化合物的药学上可接受的盐、前述化合物的氚代衍生物以及前述化合物的代谢物。还公开了包含上述物质的药物组合物、使用上述物质治疗囊性纤维化的方法以及上述物质的制造方法。