(+/-)-4-(1-nitro-2-oxocyclododecyl)butan-2-one | 129157-45-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (+/-)-4-(1-nitro-2-oxocyclododecyl)butan-2-one
• 英文别名: 4-(1'-Nitro-2'-oxocyclododecyl)-2-butanon；2-nitro-2-(3-oxobutyl)cyclododecanone；2-(3-Oxobutyl)-2-nitrocyclododecanone；2-nitro-2-(3-oxobutyl)cyclododecan-1-one
• CAS: 129157-45-5
• 化学式: C₁₆H₂₇NO₄
• 分子量: 297.395
• InChiKey: FXLBARZAGYLPBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-4-(1-nitro-2-oxocyclododecyl)butan-2-one 在 sodium tetrahydroborate 作用下， 生成 2-(3-羟基丁基)-2-硝基环十二烷-1-酮
  参考文献：
  名称：

  Design, Synthesis, and Fungicidal Activity of Macrolactones and Macrolactams with a Sulfonamide Side Chain

  摘要：

  Four series of novel macrolactones and macrolactams-12-alkylsulfonamido-1,15-pentadecanlactones (5), 12-alkylsulfonamido-15-methyl-1,15-pentadecanlactones (6), 12-alkylsulfonamido-1,15-pentadecanlactams (7), and N-(alkylsulfonamidoethyl)-l, 1 2-dodecanlactams (8)-were designed and synthesized from readily available 2-nitrocyclododecanone or cyclodoclecanone. Their structures were confirmed by 1H NIVIR, IR, and elemental analysis. The bioassay showed that these compounds displayed fair to excellent fungicidal activity against Rhizoctonia solani KOhn and have a gradual increase of fungicidal activity in the order of 6, 7, 8, and 5. Among them, compounds 5a, 5b, and 5c displayed excellent fungicidal activity against R. solani comparable with the commercial fungicide carbendazim. Above results illustrated that the rule on the relationship between the activity and hydrogen-bonding, namely the macrocyclic compounds with a hydrogen-bonding acceptor and a hydrogen-bonding donor on the ring and having a three methylenes distance between two polarizable groups have the best fungicidal activity against R. solani, has a general suitability to the macrocyclic compounds, and pesticide molecules may combine with a target enzyme by hydrogen-bonding. The facts, which compound 6 has a much lower fungicidal activity against R. solani than compound 5 but their diff erence in chemical structure is only that there is a methyl group on the C15 for compound 6 and none but hydrogen atom on the C15 for compound 5, indicated that a methyl group plays an inhibitory role to the fungicidal activity. It suggests that the existence of a methyl group with a great volume between two polarizable groups would interfere in the interaction of pesticide molecules and the target enzyme.

  DOI：

  10.1021/jf800796z
• 作为产物：
  描述：

  2-硝基环十二酮 以95%的产率得到(+/-)-4-(1-nitro-2-oxocyclododecyl)butan-2-one
  参考文献：
  名称：

  4-（1-硝基-2-氧代环十二烷基）丁烷-2-酮的意外不对称还原。（‒）-15-十六烷化物的绝对构型的测定

  摘要：

  用有机硼配合物还原4-（1-硝基-2-氧代环十二烷基）丁烷-2-酮（3）的侧链中的羰基受羰基C-在4-位的手性中心的影响带有NO 2基团的原子，一种不对称还原的稀有类型。（的独立- [R ）-或（小号）中的构型高山-氢化物，（+） - 3被减小仅给（15小号）-nitrolactone（+） - 5和，随后的转化后，向（+） -（- S）-15-十六醇化物（（+）- 1），是天然存在的（-）-的对映体1。

  DOI：

  10.1002/hlca.19890720523

文献信息

• Michael Additions in Aqueous Media: “On-Water” and “In-Water” Processes from α-Nitro Ketones and Their Anions
  作者：Giorgio Giorgi、Pilar López-Alvarado、Sonia Miranda、Jean Rodriguez、J. Carlos Menéndez

  DOI：10.1002/ejoc.201201431

  日期：2013.3

  A variety of α,β-unsaturated aldehydes and ketones gave very high-yielding Michael addition reactions with α-nitrocycloalkanones in water, at room temperature without added catalyst. These can be considered as one of the very few “on-water” Michael reactions known in the literature, because they took place in suspension or emulsion and at increased speed relative to the same transformations performed

  多种 α,β-不饱和醛和酮在室温下与水中的 α-硝基环烷酮进行高产率迈克尔加成反应，无需添加催化剂。这些可以被认为是文献中已知的极少数“水上”迈克尔反应之一，因为它们发生在悬浮液或乳液中，并且相对于在有机溶剂中进行的相同转化速度更快。使用非常稀的碳酸钾水溶液作为反应介质的相关方案将该方法的范围扩展到环烯酮和不饱和酯、腈和砜，并且很可能发生在大部分水相中，即“在水里”。这两种制备方法都是对环境友好且有效的先前已知程序的替代方法。
• ——
  作者：Yu. N. Ogibin

  DOI：10.1023/a:1023935629115

  日期：——

  A one-pot electrochemical method for the synthesis of methyl monooxoalkanoates with the carbonyl group in position 4, methyl dioxoalkanoates with the oxo groups in positions 4,7-, 6,9-, 7,10-, and 12,15, and methyl 4-oxoalkanedioates was developed. This method is based on amperostatic electrolysis in an undivided cell of the salts of esters of nitroalkanoic acids and their adducts with CH2=CHX (X = Ac, CO2Me).
• Synthesen von ?-substituierten ?-Nitrocarbons�ureestern aus ?-Nitrocycloalkanonen
  作者：Walter Huggenberg、Manfred Hesse

  DOI：10.1002/hlca.19830660519

  日期：1983.7.27

  Synthesis of ω‐Nitroalkanoates Substituted in ω‐Position from α‐Nitrocycloalkanonesα‐Nitrocycloalkanones substituted in α‐position by a functionalized alkyl residue underwent ring opening to the corresponding chain derivatives by intermolecular nucleophilic attack; ω‐nitroalkanoates substituted in ω‐position were obtained (Scheme 1). The so formed methyl 6‐nitro‐9‐oxodecanoate (3) was used to prepare methyl 8‐(2‐methyl‐1,3‐dioxolan‐2‐yl)octanoate (15), an intermediate in the synthesis of the sex phermone of the honey bee.
• STANCHEV, STEPHAN;HESSE, MANFRED, HELV. CHIM. ACTA., 72,(1989) N, C. 1052-1060
  作者：STANCHEV, STEPHAN、HESSE, MANFRED

  DOI：——

  日期：——
• STANCHEV, STEPHAN;HESSE, MANFRED, HELV. CHIM. ACTA, 73,(1990) N, C. 460-467
  作者：STANCHEV, STEPHAN、HESSE, MANFRED

  DOI：——

  日期：——